Substituted 5-hydroxy-2-phenyl-3-heteroaryl pentanenitrile derivatives, method for the production thereof and use thereof as herbicides and/or plant growth regulators

ABSTRACT

Primarily, the present invention relates to compounds of the formula (I) defined below and to their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention also relates to herbicidal or plant growth-regulating compositions comprising one or more compounds of the formula (I). Moreover, the present invention relates to processes for preparing the compounds of the formula (I).

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage entry of International ApplicationNo. PCT/EP2015/072886, filed Oct. 5, 2015, which claims priority toEuropean Patent Application No. 14188056.7, filed Oct. 8, 2014.

BACKGROUND Field

Primarily, the present invention relates to compounds of the formula (I)defined below and to their use as herbicides, in particular forcontrolling broad-leaved weeds and/or weed grasses in crops of usefulplants and/or as plant growth regulators for influencing the growth ofcrops of useful plants. The present invention also relates to herbicidalor plant growth-regulating compositions comprising one or more compoundsof the formula (I). Moreover, the present invention relates to processesfor preparing the compounds of the formula (I).

Description of Related Art

In their application, crop protection agents known to date for theselective control of harmful plants in crops of useful plants or activeingredients for controlling unwanted vegetation sometimes havedisadvantages, be it (a) that they have no or else insufficientherbicidal activity against particular harmful plants, (b) that thespectrum of harmful plants which can be controlled with an activeingredient is not wide enough, (c) that their selectivity in crops ofuseful plants is too low and/or (d) that they have a toxicologicallyunfavorable profile. Furthermore, some active ingredients which can beused as plant growth regulators for a number of useful plants causeunwanted reduced harvest yields in other useful plants or are notcompatible with the crop plant, or only within a narrow application raterange. Some of the known active ingredients cannot be producedeconomically on an industrial scale owing to precursors and reagentswhich are difficult to obtain, or they have only insufficient chemicalstabilities. In the case of other active ingredients, the activity istoo highly dependent on environmental conditions, such as weather andsoil conditions.

Inter alia, documents EP-A-0 005 341 (corresponding to U.S. Pat. No.4,224,052), EP-A-0 266 725, EP-A-0 270 830, WO 2011/098417 A1, WO2011/003775 A2, WO 2011/003776 A2, WO 2011/073143 A1, WO 2011/042378 A1,WO 2012/126764 A1, WO 2012/126765 A1, WO 2013/010882 A2, WO 2013/092500A1 and WO 2014/095879 A1 disclose herbicidal cyanobutanoic acidderivatives.

EP-A-0 005 341 describes herbicidal esters and amides of4-cyano-3,4-diphenylbutanoic acids which are optionally substituted atthe phenyl radicals. According to EP-A-0 005 341, the threo isomers aregenerally suitable for the non-selective control of harmful plants,whereas the erythro/threo isomer mixtures are suitable for the selectivecontrol of harmful plants in some crops of useful plants. Moreover,EP-A-0 005 341 mentions that the 2 enantiomers belonging to the threoform have different activities, which was investigated in an exemplarymanner on the different activities of the enantiomers of the enantiomerpair of 4-cyano-3,4-diphenylbutanoic acid unsubstituted in the phenylradicals.

EP-A-0 266 725 discloses some erythro/threo isomer mixtures which can beused selectively for controlling weeds in rice crops.

EP-A-0 270 830 describes that threo isomers and erythro/threo isomermixtures can be used as plant regulators, preventing the development ofan infructescence in various harmful grasses.

WO 2011/003775 A2 discloses specific esters of4-cyano-3,4-diphenylbutanoic acids which can be used as effectiveherbicides, preferably in crops of useful plants.

WO 2011/003776 A2, WO 2011/042378 A1, WO 2011/073143 A1, WO 2012/126764A1 and WO 2012/126765 A1 disclose 4-cyano-3,4-diphenylbutanoic acids andesters which have specific substitutions at the phenyl radicals and canbe used as effective herbicides, preferably also in crops of usefulplants.

WO 2013/010882 describes 2,3-diphenylvaleronitrile derivatives and theiruse as herbicides and plant growth regulators.

WO 2013/092500 A1 describes substituted4-cyano-3-phenyl-4-(pyridin-3-yl) butanoates, processes for theirpreparation and their use as herbicides and plant growth regulators.

WO 2014/095879 A1 describes substituted4-cyano-3-(pyridyl)-4-phenylbutanoates and their use as herbicides andplant growth regulators.

The herbicidal activity of these known compounds, in particular at lowapplication rates, and/or their compatibility with crop plants remaindeserving of improvement.

For the reasons stated, there is still a need for potent herbicidesand/or plant growth regulators for the selective use in crop plants orthe use on non-crop land, where these active ingredients preferablyshould have further advantageous properties in application, for examplewith respect to their compatibility with crop plants.

SUMMARY

It is the primary object of the present invention to provide compoundshaving herbicidal activity (herbicides) which are highly effectiveagainst economically important harmful plants even at relatively lowapplication rates and can be used selectively in crop plants, preferablywith good activity for harmful plants, and at the same time preferablyhave good compatibility with crop plants. Preferably, these herbicidalcompounds should be particularly effective and efficient against a broadspectrum of weed grasses and preferably also have good activity againsta large number of weeds.

Surprisingly, it has now been found that this object is achieved by thecompounds of the formula (I) defined below and their salts.

The present invention therefore relates to the compounds of the formula(I) and/or their salts,

in which

-   -   Q represents a mono- or bicyclic heteroaromatic radical with in        total 1 to 9 carbon ring atoms, where the heteroatom or        heteroatoms in the heteroaromatic ring are selected from the        group consisting of N, O, S, P, B, Si, and Se,    -   R¹ represents hydrogen or a hydrolyzable radical,    -   (R²)_(n) represent n substituents R², where R² (if n=1) or each        of the substituents R² (if n is greater than 1) independently of        one another represents halogen, cyano, nitro, (C₁-C₈)alkyl,        (C₁-C₈)alkoxy, (C₁-C₈)alkylthio, (C₁-C₈)alkylsulfinyl,        (C₁-C₈)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,        (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)haloalkylsulfonyl,        (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, tri[(C₁-C₄)alkyl]silyl or        tri[(C₁-C₄)alkyl]silyl(C₁-C₄)alkyl,        -   or in each case two R² directly adjacent on the            heteroaromatic radical Q are together a group of the formula            —Z¹-A*¹—Z²—, in which            -   A* represents an alkylene group having 1 to 4 carbon                atoms which is optionally substituted by one or more                radicals selected from the group consisting of halogen,                (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and                (C₁-C₄)haloalkoxy,            -   Z¹ represents a direct bond, O or S and            -   Z² represents a direct bond, O or S,        -   where the group —Z¹-A*—Z²— together with the atoms of the            heteroaromatic radical Q bonded to this group Q form a 5- or            6-membered ring (i.e. a ring with 5 or 6 ring atoms), and    -   (R³)_(m) represents m substituents R³,        -   where R³ (if m=1) or each of the substituents R³ (if m is            greater than 1) independently of one another represents            halogen, cyano, nitro, (C₁-C₈)alkyl, (C₁-C₈)alkoxy,            (C₁-C₈)alkylthio, (C₁-C₈)alkylsulfinyl,            (C₁-C₈)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,            (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio,            (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)haloalkylsulfonyl,            (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, tri[(C₁-C₄)alkyl]silyl,            tri-[(C₁-C₄)alkyl]silyl-(C₁-C₄)alkyl or —NR*R**, where R*            and R**, independently of one another and independently of            any other radicals —NR*R** present, are in each case            selected from the group consisting of H, (C₁-C₈)alkyl,            (C₂-C₈)alkenyl, (C₂-C₈)alkynyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,            (C₁-C₆)alkanoyl, [(C₁-C₄)haloalkyl]carbonyl,            [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)haloalkoxy]carbonyl,            (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl(C₁-C₄)alkyl,            (C₃-C₆)cycloalkenyl, (C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl,            phenyl and phenyl-(C₁-C₄)alkyl, where each of the specified            radicals (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl,            (C₃-C₆)cycloalkenyl, (C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl,            phenyl and phenyl-(C₁-C₄)alkyl is substituted in the cycle            optionally by one or more identical or different radicals            R^(bb), where    -   R^(bb) in each case represents halogen, (C₁-C₄)alkyl,        (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy and, in the        case of (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl,        (C₃-C₆)cycloalkenyl, (C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl, R^(bb)        may additionally represent oxo, or        -   NR*R** represents a 3- to 8-membered heterocycle which, in            addition to this nitrogen atom, optionally contains one or            two further ring heteroatoms selected from the group            consisting of N, O and S and which is unsubstituted or            substituted by one or more radicals selected from the group            consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,        -   or where in each case two groups R³ directly adjacent on the            ring together represent a group of the formula            —Z³-A^(**)-Z⁴—, in which            -   A** represents an alkylene group having 1 to 4 carbon                atoms which is optionally substituted by one or more                radicals selected from the group consisting of halogen,                (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and                (C₁-C₄)haloalkoxy,            -   Z³ represents a direct bond, O or S and            -   Z⁴ represents a direct bond, O or S,        -   where the group —Z³-A**—Z⁴ together with the carbon atoms,            bonded to this group, of the phenyl ring form a 5- or            6-membered ring,    -   n represents 0, or an integer in the range from 1 to 5,        preferably 0, 1, 2 or 3, and    -   m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 or 3.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The compounds of the formula (I) according to the invention and/or theirsalts have excellent herbicidal activity against a broad spectrum ofeconomically important mono- and dicotyledonous annual harmful plants.The compounds according to the invention also have good control overperennial harmful plants which are difficult to control and produceshoots from rhizomes, root stocks or other perennial organs.

The compounds of the formula (I) according to the invention and/or theirsalts, for example compared to the compounds described in WO 2012/126765A1, generally have more potent action at the same dosage, for exampleagainst weed grasses. Furthermore, the compounds according to theinvention have a broader spectrum of activity against weeds, i.e. thecompounds according to the invention and/or their salts can be used tocontrol effectively a relatively large number of different weeds.

The compounds of the formula (I) according to the invention and/or theirsalts have proven to be very effective in controlling harmful plantssuch as Alopecurus my osuroides, Avena fatua, Cyperus esculentus,Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilontheophrasti, Amaranthus retroflexus, Polygonum convolvulus (=Fallopiaconvolvulus), Stellaria media, Viola tricolor, and Veronica persica,where the preferred and particularly preferred compounds according tothe invention exhibited in the biological tests an 80% to 100%herbicidal action against one, several or all of the specified harmfulplants, and in so doing simultaneously more acceptable and mostly veryslight damage to the useful plant.

In addition, the compounds of the formula (I) according to the inventionand/or their salts show particularly good activity in the pre-emergencemethod, in particular against weed grasses. The pre-emergence activityof the compounds according to the invention is generally better than thepre-emergence activity of the compounds described in WO 2012/126765 A1.

Furthermore, it has been found that the compounds of the formula (I)according to the invention and/or their salts show this betterpre-emergence action particularly selectively in certain crops, inparticular in oilseed rape, soya beans, cotton and cereals (and here inparticular in maize, barley, wheat, rye, oats, triticale, milletvarieties, rice).

In general, the compounds of the formula (I) according to the inventionalso have a considerably broader activity spectrum.

In the formula (I), the formula “(R²)_(n)” means n radicals R² which areattached as substituents at the heteroaromatic radical Q, where theradicals R² in the case of n greater than 1 may be identical ordifferent and have the meaning mentioned in each case in more detail. Inthe case n=0, the heteroaromatic radical Q is not substituted bysubstituents R².

In the formula (I), the formula “(R³)_(m)” means m radicals R³ which areattached as substituents at the phenyl ring in question, where theradicals R³ in the case of n greater than 1 may be identical ordifferent and have the meaning mentioned in each case in more detail. Inthe case n=0, the phenyl ring in question is not substituted bysubstituents R³, i.e. all ring carbon atoms of the phenyl ring inpositions 2 to 6 are attached to a hydrogen atom.

In the case of R¹═H or in the case of suitable acidic substituents, thecompounds of the formula (I) are able to form salts by reaction withbases where the acidic hydrogen is replaced by an agriculturallysuitable cation.

By addition of a suitable inorganic or organic acid onto a basic group,such as, for example, amino or alkylamino, the compounds of the formula(I) are able to form salts. Suitable acidic groups present, such as, forexample, carboxylic acid groups, are able to form inner salts withgroups which for their part can be protonated, such as amino groups.

The compounds of the formula (I) may preferably be present in the formof agriculturally usable salts, where the type of salt is otherwisegenerally immaterial. In general, suitable salts are the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, have no adverse effect on the herbicidal activityof the compounds of the formula (I).

Suitable cations are in particular ions of the alkali metals, herepreferably lithium, sodium or potassium, of the alkaline earth metals,here preferably calcium or magnesium, and of the transition metals, herepreferably manganese, copper, zinc or iron. The cation used may also beammonium (NH₄ ⁺) or substituted ammonium, where one to four hydrogenatoms may be replaced here by (C₁-C₄)alkyl, hydroxy-(C₁-C₄)alkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, hydroxy (C₁-C₄)alkoxy-(C₁-C₄)alkyl, phenylor benzyl, preferred ammonium ions are ammonium, dimethylammonium,diisopropylammonium, tetramethylammonium, tetrabutylammonium,2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium,trimethylbenzylammonium. Also suitable are phosphonium ions, sulfoniumions, preferably tri-(C₁-C₄)alkylsulfonium, in particulartrimethylsulfonium, or sulfoxonium ions, preferablytri(C₁-C₄)alkylsulfoxonium, in particular trimethylsulfoxonium.

Anions of suitable acid addition salts are preferably chloride, bromide,fluoride, hydrogensulfate, sulfate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of (C₁-C₄)alkanoicacids, here in turn preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

In formula (I) and in all subsequent formulae, chemical radicals arereferred to by names which are collective terms for the enumeration ofindividual group members or specifically refer to individual chemicalradicals. Here, terms are used which are familiar to the person skilledin the art or have the meanings defined below.

A hydrolyzable radical (see definition of R¹) is a radical which can behydrolyzed under the application conditions, for example a radical whichcan be hydrolyzed even in the spray liquor or in particular under thephysiological conditions in plants, where a compound of the formula (I)where R¹ is not hydrogen is hydrolyzed to the corresponding compound ofthe formula (I) where R¹═H (hydrogen). Expressly, the definition of thehydrolyzable radicals also includes the radicals where R¹=hydrocarbonradical or heterocyclyl radical, the two last-mentioned radicals beingunsubstituted or substituted, even if some of them are hydrolyzablecomparatively slowly.

A hydrocarbon radical is an aliphatic, cycloaliphatic or aromaticmonocyclic or, in the case of an optionally substituted hydrocarbonradical, also a bicyclic or polycyclic organic radical based on theelements carbon and hydrogen, including, for example, the radicalsalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl,naphthyl, indanyl, indenyl, etc. This applies correspondingly tohydrocarbon radicals in composite meanings, such as hydrocarbonoxyradicals or other hydrocarbon radicals attached via heteroatom groups.

Unless defined in more detail, the hydrocarbon radicals preferably have1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, inparticular 1 to 12 carbon atoms.

The hydrocarbon radicals, also in the special radicals alkyl, alkoxy,haloalkyl, haloalkoxy, alkylamino and alkylthio, and also thecorresponding unsaturated and/or substituted radicals may in each casebe straight-chain or branched in the carbon skeleton.

The expression “(C₁-C₄)alkyl” is shorthand for alkyl having from 1 to 4carbon atoms, i.e. encompasses the radicals methyl, ethyl, 1-propyl,2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkylradicals having a larger specified range of carbon atoms, for example“(C₁-C₆)alkyl”, correspondingly also encompass straight-chain orbranched alkyl radicals having a greater number of carbon atoms, i.e. inthis example also the alkyl radicals having 5 and 6 carbon atoms.

Unless stated specifically or differently, preference is given to thelower carbon skeletons, for example having from 1 to 6 carbon atoms, orhaving from 2 to 6 carbon atoms in the case of unsaturated groups, inthe case of the hydrocarbon radicals such as alkyl, alkenyl and alkynylradicals, including in composite radicals. Alkyl radicals, including inthe combined definitions such as alkoxy, haloalkyl, etc., are, forexample, methyl, ethyl, n- or i-propyl, n-, t- or 2-butyl, pentyls,hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such asn-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals are defined as the possible unsaturated radicals correspondingto the alkyl radicals; alkenyl is, for example, vinyl, allyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl,2-methylpentenyl or hexenyl group, preferably allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl.

Alkenyl also includes in particular straight-chain or branchedhydrocarbon radicals having more than one double bond, such as1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenylradicals having one or more cumulated double bonds, for example allenyl(1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. Alkynyl also includes, in particular,straight-chain or branched hydrocarbon radicals having more than onetriple bond or else having one or more triple bonds and one or moredouble bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.

A 3- to 9-membered carbocyclic ring is (C₃-C₉)cycloalkyl or(C₅-C₉)cycloalkenyl.

(C₃-C₉)Cycloalkyl is a carbocyclic saturated ring system havingpreferably 3-9 carbon atoms, for example cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl or cyclononyl. In thecase of substituted cycloalkyl, cyclic systems with substituents areincluded, where the substituents may also be bonded by a double bond onthe cycloalkyl radical, for example an alkylidene group such asmethylidene.

(C₅-C₉)Cycloalkenyl is a carbocyclic, nonaromatic, partially unsaturatedring system having 5-9 carbon atoms, for example 1-cyclobutenyl,2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or1,4-cyclohexadienyl. In the case of substituted cycloalkenyl, theexplanations for substituted cycloalkyl apply correspondingly.

Alkylidene, for example also in the form of (C₁-C₁₀)alkylidene, is theradical of a straight-chain or branched alkane which is bonded via adouble bond, the position of the bonding site not being fixed. In thecase of a branched alkane, the only positions possible are, of course,those in which two hydrogen atoms can be replaced by the double bond;radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃, ═C(CH₃)—C₂H₅ or═C(C₂H₅)—C₂H₅.

“Halogen” preferably refers to the group consisting of fluorine,chlorine, bromine and iodine. Haloalkyl, -alkenyl and -alkynyl arealkyl, alkenyl and alkynyl, respectively, which are partially or fullysubstituted by identical or different halogen atoms, preferably from thegroup consisting of fluorine, chlorine and bromine, in particular fromthe group consisting of fluorine and chlorine, for examplemonohaloalkyl, perhaloalkyl, CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃,CHCl₂, CH₂CH₂Cl; haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F,CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl; this applies correspondingly tohaloalkenyl and other halogen-substituted radicals.

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl,naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyland the like, preferably phenyl.

Optionally substituted aryl also includes polycyclic systems, such astetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where thepoint of attachment is at the aromatic system.

A heterocyclic radical (heterocyclyl) comprises at least oneheterocyclic ring (=carbocyclic ring in which at least one carbon atomis replaced by a heteroatom, preferably by a heteroatom from the groupconsisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated orheteroaromatic and may be unsubstituted or substituted, where the pointof attachment is located at a ring atom. Unless defined otherwise itpreferably contains one or more, in particular 1, 2 or 3, heteroatoms inthe heterocyclic ring, preferably from the group consisting of N, O, andS; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ringatoms or a heteroaromatic radical having 5 or 6 ring atoms. Theheterocyclic radical may, for example, be a heteroaromatic radical orring (heteroaryl), such as, for example, a monocyclic, bicyclic orpolycyclic aromatic system in which at least 1 ring contains one or moreheteroatoms.

If the heterocyclyl radical or the heterocyclic ring is optionallysubstituted, it may be fused to other carbocyclic or heterocyclic rings.Preference is given to benzo-fused heterocyclic or heteroaromatic rings.

Optionally substituted heterocyclyl also includes polycyclic systems,such as, for example, 8-aza-bicyclo[3.2.1]octanyl or1-aza-bicyclo[2.2.1]heptyl. Optionally substituted heterocyclyl alsoincludes spirocyclic systems, such as, for example,1-oxa-5-aza-spiro[2.3]hexyl.

Preferably it is a radical of a heteroaromatic ring with a heteroatomfrom the group consisting of N, O, and S, for example the radical of afive- or six-membered ring such as pyridyl, pyrrolyl, thienyl or furyl;with further preference it is a radical of a correspondingheteroaromatic ring having 2, 3 or 4 heteroatoms, such as pyrimidinyl,pyridazinyl, pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl,oxazolyl, isoxazolyl, pyrazolyl, imidazolyl or triazolyl or tetrazolyl.

Here, preference is given to a radical of a heteroaromatic five- orsix-membered ring having 1 to 4 heteroatoms, such as, for example,1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,4-tetrazinyl,1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl,oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

More preference is given here to heteroaromatic radicals offive-membered heterocycles having 3 nitrogen atoms such as1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl,1,2,5-triazol-1-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-1-yl,1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl; morepreference is also given to heteroaromatic radicals of six-memberedheterocycles having 3 nitrogen atoms such as 1,3,5-triazin-2-yl,1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl,1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl; more preference is also given toheteroaromatic radicals of five-membered heterocycles having twonitrogen atoms and one oxygen atom such as 1,2,4-oxadiazol-3-yl;1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl,1,2,3-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl; more preference is alsogiven to heteroaromatic radicals of five-membered heterocycles havingtwo nitrogen atoms and one sulfur atom such as 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl,1,2,3-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl; more preference is alsogiven to heteroaromatic radicals of five-membered heterocycles havingfour nitrogen atoms such as 1,2,3,4-tetrazol-1-yl,1,2,3,4-tetrazol-5-yl, 1,2,3,5-tetrazol-1-yl, 1,2,3,5-tetrazol-4-yl,2H-1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, more preference isalso given to heteroaromatic radicals of six-membered heterocycles suchas 1,2,4,5-tetrazin-3-yl; more preference is also given toheteroaromatic radicals of five-membered heterocycles having threenitrogen atoms and one oxygen or sulfur atom such as1,2,3,4-oxatriazol-5-yl; 1,2,3,5-oxatriazol-4-yl;1,2,3,4-thiatriazol-5-yl; 1,2,3,5-thiatriazol-4-yl; more preference isalso given to heteroaromatic radicals of six-membered heterocycles suchas, for example, 1,2,4,6-thiatriazin-1-yl; 1,2,4,6-thiatriazin-3-yl;1,2,4,6-thiatriazin-5-yl.

Furthermore preferably, the heterocyclic radical or ring is a partiallyor fully hydrogenated heterocyclic radical having one heteroatom fromthe group of N, O and S, for example oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

It is also preferably a partially or fully hydrogenated heterocyclicradical having 2 heteroatoms from the group of N, O and S, for examplepiperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl and morpholinyl. Suitable substituents for a substitutedheterocyclic radical are the substituents specified later on below, andadditionally also oxo. The oxo group may also occur on the ringheteroatoms which are able to exist in different oxidation states, as inthe case of N and S, for example.

Preferred examples of heterocyclyl are a heterocyclic radical havingfrom 3 to 6 ring atoms from the group of pyridyl, thienyl, furyl,pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (=tetrahydrofuryl),pyrrolidyl, piperidyl, especially oxiranyl, 2-oxetanyl, 3-oxetanyl oroxolanyl, or is a heterocyclic radical having two or three heteroatoms,for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl,thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl,dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl ormorpholinyl.

Preferred heterocyclic radicals are also benzo-fused heteroaromaticrings, for example benzofuryl, benzisofuryl, benzothiophenyl,benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl,benzimidazolyl, benzotriazolyl, benzoxazolyl, 1,2-benzisoxazolyl,2,1-benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl,2,1-benzisothiazolyl, 1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl,1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, quinolyl (quinolinyl),isoquinolyl (isoquinolinyl), quinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl,indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and4H-benzo-1,4-dioxinyl, and, where possible, N-oxides and salts thereof.

When a base structure is substituted “by one or more radicals” from alist of radicals (=group) or a generically defined group of radicals,this in each case includes simultaneous substitution by a plurality ofidentical and/or structurally different radicals.

Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl,cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical,are, for example, a substituted radical derived from the unsubstitutedbase structure, where the substituents are, for example, one or more,preferably 1, 2 or 3, radicals from the group of halogen, alkoxy,alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido,alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- anddialkylaminocarbonyl, substituted amino such as acylamino, mono- anddialkylamino, and alkylsulfinyl, alkylsulfonyl and, in the case ofcyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl,optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; inthe term “substituted radicals”, such as substituted alkyl, etc.,substituents include, in addition to the saturatedhydrocarbon-containing radicals mentioned, corresponding unsaturatedaliphatic and aromatic radicals, such as optionally substituted alkenyl,alkynyl, alkenyloxy, alkynyloxy, phenyl and phenoxy, etc. In the case ofsubstituted cyclic radicals having aliphatic moieties in the ring,cyclic systems with those substituents which are bonded on the ring by adouble bond are also included, for example substituted by an alkylidenegroup such as methylidene or ethylidene.

The term “radicals from the group consisting of” followed by a group(list of the substituents) is, wherever used, synonymous with “radicalsselected from the group consisting of” (list of the substituents).

The substituents mentioned by way of example (“first substituent level”)may, if they contain hydrocarbonaceous moieties, optionally be furthersubstituted therein (“second substituent level”), for example by one ofthe substituents as defined for the first substituent level.Corresponding further substituent levels are possible. The term“substituted radical” preferably embraces just one or two substituentlevels.

Here, preferred substituents for the substituent levels are amino,hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide, SF₅,aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl,monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl,alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio,cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio,alkylsulfinyl, alkylsulfonyl, monoalkylaminosulfonyl,dialkylaminosulfonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl,N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy,benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino.

Two substituents together may also form a saturated or unsaturatedhydrocarbon bridge or a corresponding bridge in which carbon atoms, CHgroups or CH₂ groups are replaced by heteroatoms, thus forming afused-on or fused cycle. Here, with preference benzo-fused systems basedon the base structure are formed.

Optionally substituted phenyl is preferably unsubstituted phenyl orphenyl which is substituted by one or more radicals from the groupconsisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy-(C₁-C₄)alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio and nitro, inparticular phenyl which is optionally substituted by one or moreradicals from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl and (C₁-C₄)-alkoxy.

In the case of substituents having carbon atoms, preference is given tothose having 1 to 6 carbon atoms, preferably to those having 1 to 4carbon atoms, especially to those having 1 or 2 carbon atoms. Preferenceis generally given to substituents from the group of halogen, forexample fluorine and chlorine, (C₁-C₄)alkyl, preferably methyl or ethyl,(C₁-C₄)haloalkyl, preferably trifluoromethyl, (C₁-C₄)alkoxy, preferablymethoxy or ethoxy, (C₁-C₄)haloalkoxy, nitro and cyano. Particularpreference is given here to the substituents methyl, methoxy, fluorineand chlorine.

Substituted amino, such as mono- or disubstituted amino, is a radicalfrom the group of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals from the group of alkyl, alkoxy, acyl and aryl; preferablymono- and dialkylamino, mono- and diarylamino, acylamino,N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preferenceis given to alkyl radicals having from 1 to 4 carbon atoms; aryl ispreferably phenyl or substituted phenyl; acyl is as defined below,preferably (C₁-C₄)alkanoyl. The same applies to substitutedhydroxylamino or hydrazino.

Acyl is a radical of an organic acid which arises in a formal sense byremoval of a hydroxyl group on the acid function, and the organicradical in the acid may also be bonded to the acid function via aheteroatom. Examples of acyl are the radicals of a carboxylic acid andradicals of acids derived therefrom, such as those of thiocarboxylicacid, optionally N-substituted iminocarboxylic acids or the radical ofcarbonic monoesters, N-substituted carbamic acid, sulfonic acids,sulfinic acids, N-substituted sulfonamide acids, phosphonic acids orphosphinic acids.

Acyl is, for example, formyl, alkylcarbonyl, here preferably[(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl,N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicalsmay each for their part be substituted in the alkyl or phenyl moiety,for example in the alkyl moiety by one or more radicals from the groupof halogen, alkoxy, phenyl and phenoxy; examples of substituents in thephenyl moiety are the substituents already mentioned above in generalfor substituted phenyl.

Acyl is preferably an acyl radical in the narrower sense, i.e. a radicalof an organic acid in which the acid group is bonded directly to thecarbon atom of an organic radical, for example formyl, alkylcarbonylsuch as acetyl or [(C₁-C₄alkyl]carbonyl, phenylcarbonyl, alkylsulfonyl,alkylsulfinyl and other radicals of organic acids.

In a preferred embodiment, acyl is an alkanoyl radical having 1 to 8carbon atoms, preferably 1 to 6 carbon atoms, particularly preferably 1to 4 carbon atoms. Here, (C₁-C₄)alkanoyl is the radical of an alkanoicacid having 1 to 6 carbon atoms formed after removal of the OH group ofthe acid group, i.e. formyl, acetyl, n-propionyl, isopropionyl, n-,iso-, sec- or tert-butanoyl, n-, iso-, sec- or tert-pentanoyl, n-, iso-or sec-hexanoyl.

The “yl position” of a radical denotes the carbon atom having the freebond.

In the context of the present text, compounds of the formula (I)according to the invention and/or salts thereof are in short alsoreferred to as “compounds (I)”.

The invention also provides all stereoisomers which are encompassed byformula (I) and mixtures thereof. Compounds of the formula (I) containtwo or more asymmetric carbon atoms, and may also contain double bonds,the stereochemistry of which is not stated separately in the generalformula (I). The possible stereoisomers defined by their specificthree-dimensional shape, such as enantiomers, diastereomers, Z- andE-isomers, are all encompassed by the formula (I) and can be obtainedfrom mixtures of the stereoisomers by customary methods or else preparedby stereoselective reactions in combination with the use ofstereochemically pure starting materials.

The compounds of the formula (I) according to the invention include allstereoisomers which can occur on the basis of the centers of asymmetryor double bonds in the molecule whose configuration is not designatedspecifically in the respective structural formula or which are notspecified explicitly, and mixtures thereof, including the racemicmixtures and the mixtures enriched partly with particular stereoisomers.

The invention also provides all tautomers of the compounds of theformula (I) which may result from a hydrogen atom shift (for exampleketo-enol tautomers). The compound of the formula (I) also includes thetautomers, even if formally the formula (I) correctly describes only oneof the respective tautomers which are in equilibrium with one another orwhich can be converted into one another.

The compounds of the formula (I) also include all physical forms inwhich they may be present as a pure substance or, if appropriate, as amixture with other substances, in particular also polymorphic crystalforms of the compounds of the formula (I) and salts thereof and solventadducts (for example hydrates).

Primarily for reasons of higher herbicidal activity, better selectivityand/or better producibility, compounds of the abovementioned formula (I)according to the invention or their salts or their use according to theinvention are of particular interest in which individual radicals haveone of the preferred meanings already specified or specified below, orin particular those in which one or more of the preferred meaningsalready specified or specified below occur in combination.

Irrespective of the respective other radicals from the group consistingof R¹, (R²)_(n) and (R³)_(m) and the subdefinitions corresponding to thegeneral radicals, and preferably in combination with preferreddefinitions of one or more of these radicals, compounds according to theinvention with the preferred meanings listed below of the radicals inquestion are of particular interest.

According to the invention, preference is given to compounds of theformula (I) and/or their salts, characterized in that

-   -   Q represents a mono- or bicyclic heteroaromatic radical having        in total 2 to 9 carbon ring atoms, where the heteroaromatic        radical Q contains 1, 2, 3 or 4 heteroatoms in the        heteroaromatic ring and the heteroatom or the heteroatoms are        selected from the group consisting of N, O, and S.

According to the invention, preference is given to compounds of theformula (I) and/or their salts, characterized in that

According to the invention, further preference is given to compounds ofthe formula (I) and/or their salts, characterized in that

-   -   Q represents a mono- or bicyclic heteroaromatic radical selected        from the group consisting of pyrimidinyl, pyridinyl,        pyridazinyl, pyrazinyl, thienyl, furyl, oxazolyl, thiazolyl,        imidazolyl, pyrazolyl, triazinyl, quinolyl, isoquinolyl,        cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl, indolyl and        phthalazinyl.

Preferably, Q is a mono- or bicyclic heteroaromatic radical having intotal 3 to 9 carbon ring atoms, where at least one of the heteroatomspresent in the heteroaromatic ring is N or S, where further preferablyat least one of the heteroatoms present in the heteroaromatic ring is N.

Here, in turn preferably Q is a heteroaromatic 5- or 6-membered ring(i.e. a heteroaromatic ring with 5 or 6 ring atoms), in which preferablyall heteroatoms present in the heteroaromatic ring are N.

According to the invention, particular preference is given to compoundsof the formula (I) and/or their salts, in which Q is pyridyl,corresponding to the formulae (I-1), (I-2) and (I-3) defined below:

where

R¹, R², R³, m and n in each case have the meaning defined above orbelow.

Particularly preferred compounds of the formula (I) according to theinvention correspond to the above-defined formula (I-2), i.e. a meaningof Q particularly preferred according to the invention is 3-pyridyl.

Preference is given to compounds of the formula (I) according to theinvention or salts thereof in which

-   -   R¹ represents hydrogen or a hydrolyzable radical having a total        of up to 30 carbon atoms, preferably a hydrolyzable radical        having a total of 1 to 24 carbon atoms, preferably having a        total of 1 to 20 carbon atoms, more preferably having a total of        1 to 16 carbon atoms, particularly preferably having a total of        1 to 12 carbon atoms.

Further preference is given to compounds of the formula (I) or saltsthereof in which

-   -   R¹ represents hydrogen or a hydrolyzable radical having in total        1 to 24 carbon atoms, where R¹        -   represents an optionally substituted hydrocarbon radical or            an optionally substituted heterocyclyl radical, or        -   represents a radical of the formula SiR^(a)R^(b)R^(c), or            —NR^(a)R^(b),        -   where each of the radicals R^(a) and R^(b) independently of            the other represents hydrogen or an optionally substituted            hydrocarbon radical and R^(c) independently represents an            optionally substituted hydrocarbon radical, or —NR^(a)R^(b)            represents a 3- to 9-membered heterocycle which, in addition            to this nitrogen atom, may contain one or two further ring            heteroatoms from the group consisting of N, O and S and            which is substituted or unsubstituted, or        -   represents a radical of the formula —C(═O)—R^(e) or            —P(═O)(R^(f))₂, where R^(e) and both radicals R^(f) in each            case independently of one another are selected from the            group consisting of hydrogen, OH, unsubstituted or            substituted (C₁-C₈)alkyl, unsubstituted or substituted            (C₁-C₄)haloalkyl, unsubstituted or substituted            (C₂-C₈)alkenyl, unsubstituted or substituted (C₂-C₈)alkynyl,            unsubstituted or substituted (C₁-C₆)alkoxy, unsubstituted or            substituted (C₁-C₆)alkoxy-(C₁-C₈)alkyl, unsubstituted or            substituted (C₁-C₄)haloalkoxy, unsubstituted or substituted            (C₁-C₄)haloalkoxy-(C₁-C₈)alkyl, unsubstituted or substituted            (C₃-C₈)alkenyloxy, unsubstituted or substituted            (C₃-C₈)alkenyloxy-(C₁-C₈)alkyl, unsubstituted or substituted            (C₃-C₈)alkynyloxy, unsubstituted or substituted            (C₃-C₈)alkynyloxy-(C₁-C₈)alkyl, unsubstituted or substituted            —NR*R**, where R* and R** are as defined above,            unsubstituted or substituted tri-[(C₁-C₄)alkyl]silyl,            unsubstituted or substituted            tri-[(C₁-C₄)alkyl]silyl-(C₁-C₈)alkyl, unsubstituted or            substituted (C₃-C₆)cycloalkyl, unsubstituted or substituted            (C₃-C₆)cycloalkyl-(C₁-C₈)alkyl, unsubstituted or substituted            (C₅-C₆)cycloalkenyl, unsubstituted or substituted            (C₅-C₆)cycloalkenyl-(C₁-C₈)alkyl, unsubstituted or            substituted (C₅-C₆)cycloalkynyl, unsubstituted or            substituted (C₅-C₆)cycloalkynyl-(C₁-C₈)alkyl, unsubstituted            or substituted phenyl, unsubstituted or substituted            phenyl-(C₁-C₈)alkyl, unsubstituted or substituted phenoxy,            unsubstituted or substituted phenoxy-(C₁-C₈)alkyl,            unsubstituted or substituted phenylamino, unsubstituted or            substituted phenylamino(C₁-C₈)alkyl, unsubstituted or            substituted Het, unsubstituted or substituted            Het-(C₁-C₆)alkyl and unsubstituted or substituted            Het-O—(C₁-C₆)alkyl, where    -   Het in each case represents a saturated, partially unsaturated        or heteroaromatic monocyclic heterocyclyl radical having 3 to 9        ring atoms or a 9- or 10-membered bicyclic heterocycle in each        case containing 1, 2, 3 or 4 heteroatoms selected from the group        consisting of O, N and S, where each of the specified        substituted radicals is substituted in the acyclic moiety by one        or more identical or different radicals R^(A) and/or where each        of the specified substituted radicals is substituted in the        cyclic moiety by one or more identical or different radicals        R^(B), where    -   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)alkoxy, and    -   R^(B) independently of any further radicals R^(B) present is        selected from the group consisting of halogen, cyano, hydroxy,        oxo, nitro, (C₁-C₈)alkyl, (C₁-C₆)haloalkyl, cyano-(C₁-C₆)alkyl,        hydroxy-(C₁-C₆)alkyl, nitro-(C₁-C₆)alkyl, (C₂-C₈)alkenyl,        (C₂-C₈)haloalkenyl, (C₂-C₈)alkynyl, (C₂-C₈)haloalkynyl,        (C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy, (C₂-C₈)alkinyloxy,        (C₁-C₈)haloalkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₁-C₆)alkoxy-(C₁-C₄)alkoxy, (C₁-C₆)haloalkoxy-(C₁-C₄)alkyl,        (C₁-C₆)haloalkoxy-(C₁-C₄)alkoxy, (C₁-C₈)alkylthio,        (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio, (C₁-C₈)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₈)alkylsulfonyl,        (C₁-C₆)haloalkylsulfonyl, R^(aa)—C(═O)—,        R^(aa)—C(═O)—(C₁-C₆)alkyl, —NR*R**, tri-[(C₁-C₄)alkyl]silyl,        tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-(C₁-C₈)alkyl,        (C₃-C₈)cycloalkyl-(C₁-C₈)alkoxy, phenyl, phenyl-(C₁-C₈)alkyl,        phenoxy, phenoxy-(C₁-C₈)alkyl, phenylamino,        phenylamino-(C₁-C₈)alkyl or a 5- or 6-membered monocyclic or 9-        or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4        heteroatoms selected from the group consisting of O, N and S,        where each of these specified radicals can be substituted in the        cyclic moiety by one or more identical or different R^(bb),        where    -   R^(aa) in each case independently of one another represent        hydrogen, OH, (C₁-C₈)alkyl, (C₁-C₆)haloalkyl, (C₂-C₈)alkenyl,        (C₂-C₈)alkynyl, (C₁-C₈)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₁-C₆)alkoxy-(C₁-C₆)alkyloxy, (C₁-C₆)haloalkoxy,        (C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkoxy,        (C₃-C₈)alkenyloxy, (C₃-C₈)alkenyloxy-(C₁-C₆)alkyl,        (C₃-C₈)alkenyloxy-(C₁-C₆)alkoxy, (C₃-C₈)alkynyloxy,        (C₃-C₈)alkynyloxy-(C₁-C₆)alkyl, (C₃-C₈)alkynyloxy-(C₁-C₆)alkoxy,        —NR*R**, tri-[(C₁-C₄)alkyl]silyl,        tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,        tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkoxy, (C₃-C₈)cycloalkyl,        (C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-(C₁-C₈)alkyl,        (C₃-C₈)cycloalkyl-(C₁-C₈)alkoxy, (C₅-C₈)cycloalkenyl,        (C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl, (C₅-C₈)cycloalkenyloxy,        (C₅-C₈)cycloalkynyl, (C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl,        (C₅-C₈)cycloalkynyl-(C₁-C₆)alkoxy, phenyl, phenyl-(C₁-C₈)alkyl,        phenyl-(C₁-C₈)alkoxy, phenoxy, phenoxy-(C₁-C₈)alkyl,        phenoxy-(C₁-C₈)alkoxy, phenylamino, phenylamino-(C₁-C₈)alkyl,        phenylamino-(C₁-C₈)alkoxy or a 5- or 6-membered monocyclic or 9-        or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4        heteroatoms and optionally bonded via an alkylene group or an        alkoxy group is selected from the group consisting of O, N and        S, where each of the radicals R^(aa) encompassing a cycle is        optionally substituted in the cyclic moiety by one or more        identical or different radicals R^(bb), and

where R*, R**, —NR*R** and R^(bb) have the meaning given above.

Further preference is given to compounds of the formula (I) or saltsthereof in which

-   -   R¹ represents hydrogen, unsubstituted (C₁-C₁₈)alkyl,        unsubstituted (C₂-C₁₈)alkenyl, unsubstituted (C₂-C₁₈)alkynyl,        substituted (C₁-C₁₈)alkyl, substituted (C₂-C₁₈)alkenyl or        substituted (C₂-C₁₈)alkynyl, where in the case of substituted        (C₁-C₁₈)alkyl, substituted (C₂-C₁₈)alkenyl and substituted        (C₂-C₁₈)alkynyl the substituent(s) is/are each independently of        one another selected from groups (a)-(e) below:        -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,            (C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy, (C₂-C₈)alkynyloxy,            (C₁-C₈)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,            (C₁-C₈)alkylthio, (C₂-C₈)alkenylthio, (C₂-C₈)alkyinylthio,            (C₁-C₈)haloalkylthio, (C₂-C₈)haloalkenylthio,            (C₂-C₈)haloalkinylthio, (C₁-C₈)alkylsulfinyl,            (C₂-C₈)alkenylsulfinyl, (C₂-C₈)alkynylsulfinyl,            (C₁-C₈)haloalkylsulfinyl, (C₂-C₈)haloalkenylsulfinyl,            (C₂-C₈)haloalkinylsulfinyl, (C₁-C₈)alkylsulfonyl,            (C₂-C₈)alkenylsulfonyl, (C₂-C₈)alkynylsulfonyl,            (C₁-C₈)haloalkylsulfonyl, (C₂-C₈)haloalkenylsulfonyl,            (C₂-C₈)haloalkynylsulfonyl, —NR*R**,            -   where R*, R** and —NR*R** each have the meaning given                above,        -   (b) (C₃-C₈)cycloalkyl, (C₅-C₈)cycloalkenyl,            (C₅-C₈)cycloalkinyl, (C₃-C₈)cycloalkyl-(C₁-C₆)alkoxy,            (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl-S(O)_(p)—,            (C₅-C₈)cycloalkenyl-(C₁-C₆)alkoxy,            (C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl-S(O)_(p)—,            (C₅-C₈)cycloalkynyl-(C₁-C₆)alkoxy,            (C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl-S(O)_(p)—,            (C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-S(O)_(p)—,            (C₅-C₈)cycloalkenyloxy, (C₅-C₈)cycloalkenyl-S(O)_(p)—,            (C₅-C₈)cycloalkynyloxy, (C₅-C₈)cycloalkynyl-S(O)_(p)—,            (C₃-C₈)cycloalkoxy-(C₁-C₆)alkoxy,            (C₃-C₈)cycloalkoxy-(C₁-C₆)alkyl-S(O)_(p)—, phenyl,            phenyl(C₁-C₆)alkoxy, phenoxy, phenyl-S(O)_(p)—,            phenyl-(C₁-C₆)alkyl-S(O)_(p)—, phenoxy-(C₁-C₆)alkoxy,            phenoxy-(C₁-C₆)alkyl-S(O)_(p)—, a radical Het¹,            Het¹-S(O)_(p)—, Het¹-(C₁-C₆)alkoxy, Het¹-O—,            Het¹-O—(C₁-C₆)alkoxy, where the radical Het¹ has the meaning            given above, and where each of the last-mentioned radicals            of the group (b) in the acyclic moiety is unsubstituted or            substituted by one or more identical or different radicals            selected from the group consisting of halogen, cyano,            hydroxy and (C₁-C₆)alkoxy, and/or in the cyclic moiety is            unsubstituted or substituted by one or more identical or            different radicals R^(B), where R^(B) has the meaning given            above, and the index p is in each case 0, 1 or 2,        -   (c) —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(C),            —O—C(═O)—O—R^(C), —C(═O)—S—R^(C), —C(═S)—S—R^(C),            —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,            —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,            —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),            —P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) or            —O—P(═O)(OR^(C))(OR^(D)),            -   where R*, R** and —NR*R** each have the meaning given                above and R^(C) and R^(D) are as defined below,            -   (d) —SiR′₃, —O—SiR′₃, (R′)₃Si—(C₁-C₆)alkoxy, —CO—O—NR′₂,                —O—N═CR′₂, —N═CR′₂, —O—NR′₂, —CH(OR′)₂ and                —O—(CH₂)_(q)—CH(OR′)₂, in which each of the radicals R′                is independently selected from the group consisting of                H, (C₁-C₄)alkyl or phenyl which is unsubstituted or                substituted by one or more radicals from the group                consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,                (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy and nitro or                substituted at two adjacent positions by a                (C₂-C₆)alkylene bridge, and the index q is an integer                from 0 to 6, and            -   (e) R″O—CHR′″CH(OR″)—(C₁-C₆)alkoxy,                -   in which each of the radicals R″ independently of                    the others represents H or (C₁-C₄)alkyl or together                    the radicals represent a (C₁-C₆)alkylene group and                    R″′ represents H or (C₁-C₄)alkyl,        -   or    -   R¹ (C₃-C₉)cycloalkyl, (C₅-C₉)cycloalkenyl, (C₅-C₉)cycloalkynyl        or phenyl,        -   where each of these radicals is unsubstituted or substituted            by one or more radicals from the group consisting of the            radicals of subgroups (a′)-(e′) below:            -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,                (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,                (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₈)alkenyl,                (C₂-C₈)haloalkenyl, (C₂-C₈)alkynyl, (C₂-C₈)haloalkynyl,                (C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy, (C₂-C₈)alkynyloxy,                (C₁-C₈)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,                (C₁-C₈)alkylthio, (C₂-C₈)alkenylthio, (C₂-C₈)alkynylthio                and —NR*R**, where R*, R**, —NR*R**, and R^(bb) in each                case have the meaning given above,            -   (b′) radicals of the formulae —C(═O)—R^(C),                —C(═O)—O—R^(C), —O—C(═O)—R^(C), —O—C(═O)—O—R^(C),                —C(═O)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**,                —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C),                —N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—R^(C),                —P(═O)(R^(C))(R^(D)), —P(═O)(OR^(C))(R^(D)),                —P(═O)(OR^(C))(OR^(D)) or —O—P(═O)(OR^(C))(OR^(D)),                -   where R*, R**, —NR*R** and R^(bb) have the meaning                    given above and R^(C) and R^(D) have the meaning                    defined below,            -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,                (R′)₃Si—(C₁-C₆)alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂,                —O—NR′₂, —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR′)₂,                -   in which each of the radicals R¹ independently of                    the others represents H, (C₁-C₄)-alkyl or phenyl                    which is unsubstituted or substituted by one or more                    radicals from the group consisting of halogen,                    (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkyl,                    (C₁-C₄)haloalkoxy and nitro or is substituted at two                    adjacent positions by a (C₂-C₆)alkylene bridge, and                    q represents an integer from 0 to 6, and            -   (d′) radicals of the formula                R″O—CHR′″CH(OR″)—(C₁-C₆)alkoxy,                -   in which each of the radicals R″ independently of                    the others represents H or (C₁-C₄)alkyl or together                    the radicals represent a (C₁-C₆)alkylene group and                    R″′ represents H or (C₁-C₄)alkyl, and            -   (e′) a radical of the formula Het¹ which is                unsubstituted or substituted by one or more identical or                different radicals R^(B), where R^(B) has the meaning                given above,        -   or    -   R¹ represents a polycyclic radical based on (C₃-C₉)cycloalkyl,        (C₅-C₉)cycloalkenyl, (C₅-C₉)cycloalkynyl or phenyl, where the        base ring is fused with a carbocyclic or heterocyclic ring,        preferably a 5- or 6-membered ring having 0, 1, 2 or 3 ring        heteroatoms from the group consisting of N, O and S, preferably        benzo-fused, and where the base ring or the polycyclic system is        unsubstituted or substituted by one or more identical or        different radicals R^(B), where R^(B) has the meaning given        above,        -   is preferably unsubstituted or substituted by one or more            radicals selected from the group consisting of halogen,            cyano, nitro, hydroxy, carboxy, (C₁-C₆)alkyl,            (C₁-C₆)haloalkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl,            (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl, (C₂-C₆)alkynyl,            (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy,            (C₂-C₆)alkynyloxy, (C₁-C₆)haloalkoxy,            (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₆)alkylthio,            (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio, (C₃-C₆)cycloalkyl,            (C₃-C₆)cycloalkoxy, [(C₁-C₈)alkoxy]carbonyl,            [(C₁-C₆)haloalkoxy]carbonyl and oxo,        -   or    -   R¹ is a heterocyclic radical Het¹, which is unsubstituted in the        ring or in the polycyclic system or is substituted by one or        more identical or different radicals R^(B), where R^(B) has the        meaning given above, preferably is unsubstituted or substituted        by one or more radicals from the group halogen, cyano, thio,        nitro, hydroxy, carboxy, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy,        (C₂-C₆)alkenyloxy, (C₂-C₆)alkynyloxy, (C₁-C₆)haloalkoxy,        (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₆)alkylthio,        (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkoxy, [(C₁-C₈)alkoxy]carbonyl,        [(C₁-C₆)haloalkoxy]carbonyl and oxo,    -   where    -   Het¹ in each case independently of the others is a saturated,        partially unsaturated or heteroaromatic monocyclic heterocyclyl        radical having 3 to 9 ring atoms, preferably having 5 or 6 ring        atoms, or a 9- or 10-membered bicyclic heterocycle containing 1,        2, 3 or 4 heteroatoms selected from the group consisting of O, N        and S, preferably a 5- or 6-membered heterocycle having 1 to 3        ring heteroatoms from the group consisting of N, O and S which        is optionally also fused to a carbocyclic or heterocyclic ring,        preferably a carbocyclic ring having 3 to 6 carbon atoms or a        heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring        heteroatoms from the group consisting of N, O and S, preferably        optionally benzo-fused,    -   R^(A) has the meaning given above,    -   R^(B) has the meaning given above, and where R^(B) preferably        represents a radical selected from the group consisting of        halogen, cyano, hydroxy, oxo, nitro, (C₁-C₆)alkyl,        (C₁-C₄)haloalkyl, cyano-(C₁-C₄)alkyl, hydroxy-(C₁-C₄)alkyl,        nitro-(C₁-C₄)alkyl, (C₂-C₆)alkenyl, (C₂-C₆)haloalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy,        (C₂-C₆)alkenyloxy, (C₂-C₆)alkynyloxy, (C₁-C₆)haloalkoxy,        (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkoxy,        (C₁-C₆)alkylthio, (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio,        (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl,        (C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylsulfonyl, a radical of the        formula ^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)alkyl, where R^(aa)        has the meaning given above, —NR*R**, where R*, R**, —NR*R**,        and R^(bb) in each case have the meaning given above,        tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,        (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkoxy,        (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkyl-(C₁-C₈)alkoxy,        phenyl, phenyl-(C₁-C₆)alkyl, phenoxy, phenoxy-(C₁-C₆)alkyl,        phenylamino, phenylamino-(C₁-C₆)alkyl, or a 5- or 6-membered        monocyclic or 9- or 10-membered bicyclic heterocycle containing        1, 2, 3 or 4 heteroatoms selected from the group consisting of        O, N and S, where each of the radicals R^(B) in the cyclic        moiety is optionally substituted by one or more identical or        different radicals R^(bb), where R^(B) and R^(bb) in each case        have the meaning given above,    -   R^(C) and R^(D) each independently of one another (and also        independently of radicals R^(C), R^(D) in other groups)        represent a radical selected from the group consisting of:        -   (i) hydrogen, unsubstituted (C₁-C₈)alkyl, unsubstituted            (C₂-C₈)alkenyl, unsubstituted (C₂-C₈)alkynyl, substituted            (C₁-C₈)alkyl, substituted (C₂-C₈)alkenyl, and substituted            (C₂-C₈)alkynyl, where each of these substituted radicals is            substituted by one or more radicals from the group halogen,            cyano, nitro, hydroxy, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy,            (C₂-C₆)alkynyloxy, (C₁-C₈)haloalkoxy,            (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₈)alkylthio,            (C₁-C₈)haloalkylthio, (C₁-C₈)alkylsulfinyl,            (C₁-C₈)haloalkylsulfinyl, (C₁-C₈)alkylsulfonyl,            (C₁-C₈)haloalkylsulfonyl and tri-[(C₁-C₄)alkyl]silyl,        -   and        -   (ii) (C₃-C₈)cycloalkyl, (C₅-C₈)cycloalkenyl,            (C₅-C₈)cycloalkynyl, phenyl, (C₃-C₈)cycloalkyl-(C₁-C₆)alkyl,            (C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl,            (C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl, phenyl-(C₁-C₆)alkyl,            (C₃-C₈)cycloalkyloxy-(C₁-C₆)alkyl,            (C₃-C₈)cycloalkyl-S(O)_(p)—(C₁-C₆)alkyl,            (C₅-C₈)cycloalkenyloxy-(C₁-C₆)alkyl,            (C₅-C₈)cycloalkynyloxy-(C₁-C₆)alkyl, phenoxy-(C₁-C₆)alkyl,            phenyl-S(O)_(p)—(C₁-C₆)alkyl,            (C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl,            (C₅-C₈)cycloalkenylamino-(C₁-C₆)alkyl,            (C₅-C₈)cycloalkynylamino-(C₁-C₆)alkyl,            phenylamino-(C₁-C₆)alkyl, Het¹, Het¹-(C₁-C₆)alkyl,            Het¹-O—(C₁-C₆)alkyl or Het¹-S(O)_(p)—(C₁-C₆)alkyl, where            Het¹ has the meaning given above, and where each of these            radicals is unsubstituted in the acyclic moiety or            substituted by one or more identical or different radicals            R^(A) and in the cyclic moiety is unsubstituted or            substituted by one or more identical or different radicals            R^(B) and p in each case represents 0, 1 or 2, where R^(A)            and R^(B) in each case have the meaning given above,    -   R^(aa) has the meaning given above, and where R^(aa) preferably        independently is a radical selected from the group consisting of        hydrogen, OH, (C₁-C₆)alkyl, (C₁-C₄)haloalkyl, (C₂-C₆)alkenyl,        (C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,        (C₁-C₆)alkoxy-(C₁-C₆)alkyloxy, (C₁-C₄)haloalkoxy,        (C₁-C₄)haloalkoxy-(C₁-C₆)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₆)alkoxy,        (C₃-C₆)alkenyloxy, (C₃-C₆)alkenyloxy-(C₁-C₆)alkyl,        (C₃-C₆)alkenyloxy-(C₁-C₆)alkoxy, (C₃-C₆)alkynyloxy,        (C₃-C₆)alkynyloxy-(C₁-C₆)alkyl, (C₃-C₆)alkynyloxy-(C₁-C₆)alkoxy,        —NR*R**, where R* and R** are as defined above,        tri[(C₁-C₄)alkyl]silyl, tri[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,        tri[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkoxy, (C₃-C₆)cycloalkyl,        (C₃-C₆)cycloalkoxy, (C₃-C₆)cycloalkyl-(C₁-C₈)alkyl,        (C₃-C₆)cycloalkyl-(C₁-C₈)alkoxy, (C₅-C₆)cycloalkenyl,        (C₅-C₆)cycloalkenyl-(C₁-C₆)alkyl, (C₅-C₆)cycloalkenyloxy,        (C₅-C₆)cycloalkynyl, (C₅-C₆)cycloalkynyl-(C₁-C₆)alkyl,        (C₅-C₆)cycloalkynyl-(C₁-C₆)alkoxy, phenyl, phenyl-(C₁-C₆)alkyl,        phenyl-(C₁-C₆)alkoxy, phenoxy, phenoxy-(C₁-C₆)alkyl,        phenoxy-(C₁-C₆)alkoxy, phenylthio, phenyl-S(O)_(p)—(C₁-C₆)alkyl,        phenyl-S(O)_(p)—(C₁-C₆)alkoxy, where p in each case        independently of one another is 0, 1 or 2, phenylamino,        phenylamino-(C₁-C₆)alkyl, phenylamino-(C₁-C₆)alkoxy or a 5- or        6-membered monocyclic or 9- or 10-membered bicyclic heterocycle        optionally bonded via an alkylene group or an alkoxy group,        containing 1, 2, 3 or 4 heteroatoms selected from the group        consisting of O, N and S, where each of the specified cyclic        radicals R^(aa) in the cyclic moiety is optionally substituted        by one or more identical or different radicals selected from the        group consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)alkoxy and (C₁-C₄)haloalkoxy.

For reasons of stronger herbicidal activity, better selectivity andbetter or easier handling, inter alia, compounds of the formula (I)according to the invention and/or salts thereof in which R¹═H(hydrogen), preferably compounds of the formula (Ia) defined below, areparticularly preferable in the context of the present invention.

Particular preference is likewise given to compounds of the formula (I)according to the invention and/or salts thereof which, under applicationconditions, comparatively easily lead to a compound of the formula (I)where R¹═H, for example by degradation or hydrolysis.

In this case, the actual structure of group R¹ is not critical, where—asmentioned—preferably under the application conditions—for example by(enzymatic) degradation, cleavage or hydrolysis—at least to some extenta compound of the formula (I) where R¹═H, corresponding to a compound ofthe formula (Ia) defined below, is formed.

In the context of what was discussed above, in a preferred aspect R¹represents hydrogen or a group selected from the group consisting of—C(═O)—R^(C), —C(═O)—O—R^(C), —C(═O)—S—R^(C), —C(═S)—S—R^(C) and—C(═O)—NR*R**, particularly preferably hydrogen or a group —C(═O)—R^(C),where R^(C), R* and R** each have the meaning defined above, preferablyeach have one of the meanings given above as being preferred.

Especially preferably, R¹ represents hydrogen or a group selected fromthe group consisting of —C(═O)—R^(C) and —C(═O)—O—R^(C), here in turnparticularly preferably hydrogen or —C(═O)—R^(C), where R^(C) preferablycomprises a total of 1 to 16 carbon atoms, with preference a total of 1to 12 carbon atoms.

Particularly preferably, R^(C) in each case particularly preferablyrepresents a radical selected from the group consisting of:

(i) hydrogen, unsubstituted (C₁-C₈)alkyl, unsubstituted (C₂-C₈)alkenyl,unsubstituted (C₂-C₈)alkynyl, substituted (C₁-C₈)alkyl, substituted(C₂-C₈)alkenyl, and substituted (C₂-C₈)alkynyl, where each of thesesubstituted radicals is substituted by one or more radicals from thegroup halogen, cyano, hydroxy, (C₁-C₄)alkoxy, (C₂-C₆)alkenyloxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl,(C₁-C₈)haloalkylsulfonyl and tri [(C₁-C₄)alkyl]silyl,

and

(ii) (C₃-C₈)cycloalkyl, (C₅-C₈)cycloalkenyl, phenyl,phenyl-(C₁-C₆)alkyl, (C₃-C₈)cycloalkyloxy-(C₁-C₆)alkyl,phenoxy-(C₁-C₆)alkyl, Het¹, Het¹-(C₁-C₆)alkyl, Het¹-O—(C₁-C₆)alkyl,where Het¹ has the meaning mentioned above and where each of theseradicals in the acyclic moiety is unsubstituted or substituted by one ormore identical or different radicals R^(A) and in the cyclic moiety isunsubstituted or substituted by one or more identical or differentradicals R^(B), where R^(A) and R^(B) in each case have the meaninggiven above, where in turn preferably R^(A) and R^(B) have the followingmeaning:

-   -   R^(A) independently of any other radicals R^(A) present is        selected from the group consisting of halogen, cyano, hydroxy        and (C₁-C₄)alkoxy, and    -   R^(B) independently of any other radicals R^(B) present is        selected from the group consisting of halogen, cyano, hydroxy,        nitro, (C₁-C₆)alkyl, (C₁-C₆)haloalkyl, cyano-(C₁-C₆)alkyl,        hydroxy-(C₁-C₆)alkyl, (C₂-C₈)alkenyl, (C₂-C₈)haloalkenyl,        (C₂-C₆)alkynyl, (C₂-C₆)haloalkynyl, (C₁-C₆)alkoxy,        (C₂-C₆)alkenyloxy, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkoxy-(C₁-C₄)alkyl, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₄)haloalkoxy-(C₁-C₄)alkoxy,        (C₁-C₆)alkylthio, (C₂-C₆)alkenylthio, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl, and        (C₁-C₆)haloalkylsulfonyl,

where R^(C) preferably comprises a total of 1 to 16 carbon atoms, withpreference a total of 1 to 12 carbon atoms.

In formula (I), especially preferably R¹ represents hydrogen,—C(═O)—O—R^(C) or —C(═O)—R^(C), where the group R^(C) is in each caseselected from the group consisting of:

(i) unsubstituted (C₁-C₆)alkyl, unsubstituted (C₂-C₆)alkenyl,unsubstituted (C₂-C₆)alkynyl, substituted (C₁-C₆)alkyl, substituted(C₂-C₆)alkenyl and substituted (C₂-C₆)alkynyl, where each of thesesubstituted radicals is substituted by one or more radicals from thegroup consisting of methyl, hydroxy, fluorine and chlorine,

(ii) (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyloxy-(C₁-C₄)alkyl, phenyl, whereeach of these radicals in the cyclic moiety is unsubstituted orsubstituted by one or more identical or different radicals R^(B), whereR^(B) independently of any other radicals R^(B) present is selected fromthe group consisting of halogen (here preferably fluorine, chlorine,bromine), cyano, nitro and (C₁-C₄)alkyl (here in turn preferablymethyl), where R^(C) preferably comprises a total of 1 to 12 carbonatoms, with preference a total of 1 to 10 carbon atoms.

In formula (I), R¹ especially preferably represents hydrogen or a groupselected from the group consisting of: acetyl, propanoyl, butanoyl,pentanoyl, hexanoyl, 2-methylpropanoyl (=isopropanoyl),2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe,cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl,but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl,2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl,2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl, 2-nitrobenzoyl,2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2,2-dichloroacetyl,2-methoxyacetyl, 2,6-difluorobenzoyl, C(O)C(═O)OMe and C(O)CH₂C(O)OMe.

Preferred compounds according to the invention are, therefore, compoundsof the formula (I), in which R¹ has the meaning given in Table U1 below(see Example Section).

In formula (I), R¹ especially preferably represents hydrogen or a groupselected from the group consisting of:

acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl(=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe,cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl,but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl,2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl,2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl and2-nitrobenzoyl.

Further preference is given to compounds of the formula (I) according tothe invention or salts thereof in which

-   -   (R²)_(n) represents n substituents R²,        -   where R₂ (if n=1) or each of the substituents R² (if n is            greater than 1) independently of the others represents            halogen, cyano, nitro, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,            (C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl,            (C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,            (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio,            (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)haloalkylsulfonyl,            (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, tri[(C₁-C₄)alkyl]silyl or            tri[(C₁-C₄)alkyl]silyl-(C₁-C₄)alkyl,        -   and/or    -   (R³)_(m) represents m substituents R³,        -   where R³ (if m=1) or each of the substituents R³ (if m is            greater than 1) independently of the others represents            halogen, cyano, nitro, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,            (C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl,            (C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,            (C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio,            (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)haloalkylsulfonyl,            (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, NR*R**,            tri[(C₁-C₄)alkyl]silyl or            tri[(C₁-C₄)alkyl]silyl(C₁-C₄)alkyl,        -   or where in each case two groups R³ directly adjacent on the            ring together represent a group of the formula —Z³-A**—Z⁴,            in which            -   A** represents an alkylene group having 1 to 4 carbon                atoms which is optionally substituted by one or more                radicals from the group consisting of halogen,                (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and                (C₁-C₄)haloalkoxy,            -   Z³ represents a direct bond, O or S and            -   Z⁴ represents a direct bond, O or S,        -   where the group —Z³-A**—Z⁴ together with the carbon atoms,            attached to the group, of the phenyl ring form a fused-on 5-            or 6-membered ring,    -   R*, R** each independently of one another or together with the        nitrogen atom have the meaning given above,    -   n, m in each case independently of one another are 0, 1, 2, 3, 4        or 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2,

where in addition preferably

R¹ is hydrogen or a group selected from the group consisting of:

acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl, 2-methylpropanoyl(=isopropanoyl), 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl, C(═O)OMe,cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl,but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl,2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl, 2-fluorobenzoyl,2,2-dimethylpropanoyl (=pivaloyl), 3,3-dimethylbutanoyl, 2-nitrobenzoyl,2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2,2-dichloroacetyl,2-methoxyacetyl, 2,6-difluorobenzoyl, C(O)C(═O)OMe and C(O)CH₂C(O)OMe.

Further preference is given to compounds of the formula (I) according tothe invention or salts thereof or of the formula (Ia) defined below orsalts thereof, in which

-   -   (R²)_(n) represents n substituents R²,        -   where, in the case that n=1, the substituent R² or, in the            case that n is greater than 1, each of the substituents R²            independently of the others represents        -   halogen, cyano, nitro, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,            (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,            (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl,            (C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio,            (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)haloalkylsulfonyl,            (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, tri[(C₁-C₄)alkyl]silyl or            tri[(C₁-C₄)alkyl]silyl (C₁-C₄)alkyl and        -   n represents 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, in            particular 0, 1 or 2,    -   and/or    -   (R³)_(m) represents m substituents R³,        -   where in the case that m=1, the substituent R³ or, in the            case that m is greater than 1, each of the substituents R³            independently of one another represents halogen, cyano,            nitro, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,            (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl,            (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl, (C₁-C₄)haloalkoxy,            (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,            (C₁-C₄)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl or            tri-[(C₁-C₄)alkyl]silyl-Z^(b)—, where Z^(b)═ is a covalent            bond or (C₁-C₄)alkylene, or        -   in each case two groups R³ directly adjacent to one another            at the ring together represent a group of the formula            —Z³-A**-Z        -   where            -   A** represents an alkylene group which is optionally                substituted by one or more radicals from the group                halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy                and (C₁-C₄)haloalkoxy,            -   Z³ represents O or S and            -   Z⁴ represents O or S, where the group —Z³-A**—Z⁴                together with the carbon atoms, attached to the group,                of the phenyl ring form a fused-on 5- or 6-membered                ring,    -   m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in        particular 0, 1, 2 or 3.

Further preference is given to compounds of the formula (I) according tothe invention or salts thereof or of the formula (Ia) defined below orsalts thereof, in which

-   -   (R²)_(n) represents n substituents R²,        -   where, in the case that n=1, the substituent R² or, in the            case that n is greater than 1, each of the substituents R²            independently of one another represents fluorine, chlorine,            bromine, iodine, cyano, nitro, methyl, ethyl, methoxy,            methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl,            trifluoromethoxy, trifluoroalkylthio,            trifluoromethylsulfinyl or trifluoromethylsulfonyl, and    -   (R³)_(m) represents m substituents R³,        -   where, in the case that m=1, the substituent radical R³ or,            in the case that m is greater than 1, each of the            substituents R³ independently of one another represents            fluorine, chlorine, bromine, iodine, cyano, nitro, methyl,            methoxy, (here preferably 2-methoxy, 3-methoxy), methylthio,            methylsulfinyl, methylsulfonyl, trifluoromethyl,            trifluoromethoxy, trifluoroalkylthio,            trifluoromethylsulfinyl or trifluoromethylsulfonyl, and    -   m represents 0, 1, 2, 3 or 4, preferably 0, 1, 2 or 3, and    -   n represents 0, 1, 2 or 3, preferably 0, 1 or 2,

and also preferably

-   -   R¹ is hydrogen or a group selected from the group consisting of:        acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl,        2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl,        2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl,        1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl,        2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl,        2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl,        2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl),        3,3-dimethylbutanoyl and 2-nitrobenzoyl.

Particular preference is given to compounds of the formula (I) accordingto the invention or salts thereof or of the formula (Ia) defined belowor salts thereof, in which

-   -   (R²)_(n) represents n substituents R², where, in the case that        n=1, the substituent R² or, in the case that n is greater than        1, each of the substituents R² independently of the others is        fluorine, chlorine, bromine, iodine, cyano, nitro, methyl,        ethyl, or methoxy.

Particular preference is given to compounds of the formula (I) accordingto the invention or salts thereof or of the formula (Ia) defined belowor salts thereof, in which

-   -   (R³)_(m) represents m substituents R³, 2-bromo, 3-bromo,        4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro,        4-fluoro, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl,        4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF₃, 3-CF₃, 4-CF₃,        2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy,        2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl,        3-methylsulfinyl, 4-methylsulfinyl, 2-methylsulfonyl,        3-methylsulfonyl, 4-methylsulfonyl, 2-nitro, 3-nitro, 4-nitro,        2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl,        3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro, 2,4-difluoro,        2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro,        2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro,        3,4-dichloro, 3,5-dichloro, 2,5-dicyano, 2,6-dicyano,        (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F),        (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F),        (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4-NO₂-3-F), (4-OMe-3-F),        (3-Br-4-F), (3-CN-4-F), (3-NO₂-4-F), (3-CN-4-Cl), (3-NO₂-4-Cl),        (5-CN-2-F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro,        2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro,        2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro,        3,4,5-trichloro or (2,6-F₂-4-Cl).

Preferred compounds according to the invention are compounds of theformula (Ia) shown below, (corresponding to compounds of the formula (I)in which the radical R¹=hydrogen), their salts and their esters

in which Q, R², R³, m and n in each case have the meanings given aboveand below, with preference the meanings stated as preferred, preferablythe meanings stated as preferred, particularly preferably the meaningsstated as preferred, and especially (preferably) the meanings stated asespecially (preferred).

In a preferred embodiment of the present invention, m+n>0, i.e.preferably at least one of the radicals R² and R³ does not representhydrogen.

Preference according to the invention is given to compounds of theformula (I) or (Ia) or salts thereof in which n>0.

Preference according to the invention is likewise given to compounds ofthe formula (I) or (Ia) or salts thereof in which m>0.

In a preferred embodiment of the present invention, m+n>1, i.e.preferably at least two radicals R², at least two radicals R³ or atleast one radical R² and at least one radical R³ do not representhydrogen.

In preferred compounds of the formula (I) or (Ia) according to theinvention or salts thereof, the sum of m+n=2, 3, 4 or 5.

In particularly preferred compounds of the formula (I) or (Ia) accordingto the invention, n is greater than or equal to 1 and one or moreradicals R² represent halogen, preferably halogen selected from thegroup consisting of F, Cl and Br.

In particularly preferred compounds of the formula (I) or (Ia) accordingto the invention, m is greater than or equal to 1 and one or moreradicals R³ represent halogen, preferably halogen from the groupconsisting of F, Cl and Br.

Particularly preferred compounds of the formula (Ia) according to theinvention correspond to the above-defined formula (I-2), in whichR¹=hydrogen.

Particular preference is likewise given to compounds of the formula (I)according to the invention or salts thereof in which

-   -   (R²)_(n) represents n substituents R²,        -   where, in the case that n=1, the substituent R² or, in the            case that n is greater than 1, each of the substituents R²            independently of the others is fluorine, chlorine, bromine,            iodine, cyano, nitro, methyl, ethyl, or methoxy,    -   (R³)_(m) represents m substituents R³, where, in the case that        m=1, the substituent radical R³ or, in the case that m is        greater than 1, each of the substituents R³ independently of the        others is 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro,        4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano,        4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl,        4-ethyl, 2-CF₃, 3-CF₃, 4-CF₃, 2-methoxy, 3-methoxy, 4-methoxy,        2-ethoxy, 3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio,        4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl,        4-methylsulfinyl, 2-methylsulfonyl, 3-methylsulfonyl,        4-methylsulfonyl, 2-nitro, 3-nitro, 4-nitro, 2,3-dimethyl,        2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl,        3,5-dimethyl, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro,        2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro,        2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro,        3,5-dichloro, 2,5-dicyano, 2,6-dicyano, (2-Cl-3-F), (2-Cl-4-F),        (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),        (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F),        (4-CN-3-F), (4-NO₂-3-F), (4-OMe-3-F), (3-Br-4-F), (3-CN-4-F),        (3-NO₂-4-F), (3-CN-4-Cl), (3-NO₂-4-Cl), (S—CN-2-F),        2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro,        2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro,        2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro,        3,4,5-trichloro or (2,6-F₂-4-Cl),    -   R¹ is hydrogen or a group selected from the group consisting of:        acetyl, propanoyl, butanoyl, pentanoyl, hexanoyl,        2-methylpropanoyl (=isopropanoyl), 2,2-difluoroacetyl,        2,2,2-trifluoroacetyl, C(═O)OMe, cyclopropanecarbonyl,        1-methylcyclopropanecarbonyl, acryl, prop-2-ynoyl, but-2-ynoyl,        2-methylacryl, benzoyl, 4-chlorobenzoyl, 3-chlorobenzoyl,        2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl,        2-fluorobenzoyl, 2,2-dimethylpropanoyl (=pivaloyl),        3,3-dimethylbutanoyl and 2-nitrobenzoyl,    -   m is 0, 1, 2 or 3, and    -   n is 0, 1 or 2,

where preferably the sum of m+n=2, 3, 4, or 5.

Preferred compounds according to the invention are compounds of theformula (I) or (Ia), in which Q(R²)_(n) has the meaning given in Table 1below.

Preferred compounds according to the invention are compounds of theformula (I) or (Ia), in which (R³)_(n) has the meaning given in Table 1below.

Preferred compounds according to the invention are compounds of theformula (I) or of the formula (Ia) as defined in Table 1 below.

Table 1 below gives preferred meanings of Q(R²)_(n) and (R³)_(m). Theabbreviations and annotations used herein are explained in the ExampleSection.

TABLE 1 Preferred meanings of Q(R²)_(n) and (R³)_(m) in compounds of theformula (I) or of the formula (Ia) according to the invention: No.Q(R²)_(n) (R³)_(m) 1 6-fluoropyridin-2-yl H 2 6-fluoropyridin-2-yl 2-F 36-fluoropyridin-2-yl 3-F 4 6-fluoropyridin-2-yl 4-F 56-fluoropyridin-2-yl 3-Cl 6 6-fluoropyridin-2-yl 4-Cl 76-fluoropyridin-2-yl 3-Br 8 6-fluoropyridin-2-yl 4-Br 96-fluoropyridin-2-yl 3-I 10 6-fluoropyridin-2-yl 3-CN 116-fluoropyridin-2-yl 4-CN 12 6-fluoropyridin-2-yl 3-NO₂ 136-fluoropyridin-2-yl 3-Me 14 6-fluoropyridin-2-yl 4-Me 156-fluoropyridin-2-yl 2,3-F₂ 16 6-fluoropyridin-2-yl 2,4-F₂ 176-fluoropyridin-2-yl 2,5-F₂ 18 6-fluoropyridin-2-yl 2,6-F₂ 196-fluoropyridin-2-yl 3,4-F₂ 20 6-fluoropyridin-2-yl 3,5-F₂ 216-fluoropyridin-2-yl 3,4,5-F₃ 22 6-fluoropyridin-2-yl 3-F, 4-Cl 236-fluoropyridin-2-yl 3-F, 4-Br 24 6-fluoropyridin-2-yl 3-CN, 4-F 256-fluoropyridin-2-yl 3-Br, 4-F 26 6-fluoropyridin-2-yl 3-Cl, 4-F 276-fluoropyridin-2-yl 3,4-Cl₂ 28 5-fluoropyridin-2-yl H 295-fluoropyridin-2-yl 2-F 30 5-fluoropyridin-2-yl 3-F 315-fluoropyridin-2-yl 4-F 32 5-fluoropyridin-2-yl 3-Cl 335-fluoropyridin-2-yl 4-Cl 34 5-fluoropyridin-2-yl 3-Br 355-fluoropyridin-2-yl 4-Br 36 5-fluoropyridin-2-yl 3-I 375-fluoropyridin-2-yl 3-CN 38 5-fluoropyridin-2-yl 4-CN 395-fluoropyridin-2-yl 3-NO₂ 40 5-fluoropyridin-2-yl 3-Me 415-fluoropyridin-2-yl 4-Me 42 5-fluoropyridin-2-yl 2,3-F₂ 435-fluoropyridin-2-yl 2,4-F₂ 44 5-fluoropyridin-2-yl 2,5-F₂ 455-fluoropyridin-2-yl 2,6-F₂ 46 5-fluoropyridin-2-yl 3,4-F₂ 475-fluoropyridin-2-yl 3,5-F₂ 48 5-fluoropyridin-2-yl 3,4,5-F₃ 495-fluoropyridin-2-yl 3-F, 4-Cl 50 5-fluoropyridin-2-yl 3-F, 4-Br 515-fluoropyridin-2-yl 3-CN, 4-F 52 5-fluoropyridin-2-yl 3-Br, 4-F 535-fluoropyridin-2-yl 3-Cl, 4-F 54 5-fluoropyridin-2-yl 3,4-Cl₂ 554-fluoropyridin-2-yl H 56 4-fluoropyridin-2-yl 2-F 574-fluoropyridin-2-yl 3-F 58 4-fluoropyridin-2-yl 4-F 594-fluoropyridin-2-yl 3-Cl 60 4-fluoropyridin-2-yl 4-Cl 614-fluoropyridin-2-yl 3-Br 62 4-fluoropyridin-2-yl 4-Br 634-fluoropyridin-2-yl 3-I 64 4-fluoropyridin-2-yl 3-CN 654-fluoropyridin-2-yl 4-CN 66 4-fluoropyridin-2-yl 3-NO₂ 674-fluoropyridin-2-yl 3-Me 68 4-fluoropyridin-2-yl 4-Me 694-fluoropyridin-2-yl 2,3-F₂ 70 4-fluoropyridin-2-yl 2,4-F₂ 714-fluoropyridin-2-yl 2,5-F₂ 72 4-fluoropyridin-2-yl 2,6-F₂ 734-fluoropyridin-2-yl 3,4-F₂ 74 4-fluoropyridin-2-yl 3,5-F₂ 754-fluoropyridin-2-yl 3,4,5-F₃ 76 4-fluoropyridin-2-yl 3-F, 4-Cl 774-fluoropyridin-2-yl 3-F, 4-Br 78 4-fluoropyridin-2-yl 3-CN, 4-F 794-fluoropyridin-2-yl 3-Br, 4-F 80 4-fluoropyridin-2-yl 3-Cl, 4-F 814-fluoropyridin-2-yl 3,4-Cl₂ 82 3-fluoropyridin-2-yl H 833-fluoropyridin-2-yl 2-F 84 3-fluoropyridin-2-yl 3-F 853-fluoropyridin-2-yl 4-F 86 3-fluoropyridin-2-yl 3-Cl 873-fluoropyridin-2-yl 4-Cl 88 3-fluoropyridin-2-yl 3-Br 893-fluoropyridin-2-yl 4-Br 90 3-fluoropyridin-2-yl 3-I 913-fluoropyridin-2-yl 3-CN 92 3-fluoropyridin-2-yl 4-CN 933-fluoropyridin-2-yl 3-NO₂ 94 3-fluoropyridin-2-yl 3-Me 953-fluoropyridin-2-yl 4-Me 96 3-fluoropyridin-2-yl 2,3-F₂ 973-fluoropyridin-2-yl 2,4-F₂ 98 3-fluoropyridin-2-yl 2,5-F₂ 993-fluoropyridin-2-yl 2,6-F₂ 100 3-fluoropyridin-2-yl 3,4-F₂ 1013-fluoropyridin-2-yl 3,5-F₂ 102 3-fluoropyridin-2-yl 3,4,5-F₃ 1033-fluoropyridin-2-yl 3-F, 4-Cl 104 3-fluoropyridin-2-yl 3-F, 4-Br 1053-fluoropyridin-2-yl 3-CN, 4-F 106 3-fluoropyridin-2-yl 3-Br, 4-F 1073-fluoropyridin-2-yl 3-Cl, 4-F 108 3-fluoropyridin-2-yl 3,4-Cl₂ 1096-chloropyridin-2-yl H 110 6-chloropyridin-2-yl 2-F 1116-chloropyridin-2-yl 3-F 112 6-chloropyridin-2-yl 4-F 1136-chloropyridin-2-yl 3-Cl 114 6-chloropyridin-2-yl 4-Cl 1156-chloropyridin-2-yl 3-Br 116 6-chloropyridin-2-yl 4-Br 1176-chloropyridin-2-yl 3-I 118 6-chloropyridin-2-yl 3-CN 1196-chloropyridin-2-yl 4-CN 120 6-chloropyridin-2-yl 3-NO₂ 1216-chloropyridin-2-yl 3-Me 122 6-chloropyridin-2-yl 4-Me 1236-chloropyridin-2-yl 2,3-F₂ 124 6-chloropyridin-2-yl 2,4-F₂ 1256-chloropyridin-2-yl 2,5-F₂ 126 6-chloropyridin-2-yl 2,6-F₂ 1276-chloropyridin-2-yl 3,4-F₂ 128 6-chloropyridin-2-yl 3,5-F₂ 1296-chloropyridin-2-yl 3,4,5-F₃ 130 6-chloropyridin-2-yl 3-F, 4-Cl 1316-chloropyridin-2-yl 3-F, 4-Br 132 6-chloropyridin-2-yl 3-CN, 4-F 1336-chloropyridin-2-yl 3-Br, 4-F 134 6-chloropyridin-2-yl 3-Cl, 4-F 1356-chloropyridin-2-yl 3,4-Cl₂ 136 5-chloropyridin-2-yl H 1375-chloropyridin-2-yl 2-F 138 5-chloropyridin-2-yl 3-F 1395-chloropyridin-2-yl 4-F 140 5-chloropyridin-2-yl 3-Cl 1415-chloropyridin-2-yl 4-Cl 142 5-chloropyridin-2-yl 3-Br 1435-chloropyridin-2-yl 4-Br 144 5-chloropyridin-2-yl 3-I 1455-chloropyridin-2-yl 3-CN 146 5-chloropyridin-2-yl 4-CN 1475-chloropyridin-2-yl 3-NO₂ 148 5-chloropyridin-2-yl 3-Me 1495-chloropyridin-2-yl 4-Me 150 5-chloropyridin-2-yl 2,3-F₂ 1515-chloropyridin-2-yl 2,4-F₂ 152 5-chloropyridin-2-yl 2,5-F₂ 1535-chloropyridin-2-yl 2,6-F₂ 154 5-chloropyridin-2-yl 3,4-F₂ 1555-chloropyridin-2-yl 3,5-F₂ 156 5-chloropyridin-2-yl 3,4,5-F₃ 1575-chloropyridin-2-yl 3-F, 4-Cl 158 5-chloropyridin-2-yl 3-F, 4-Br 1595-chloropyridin-2-yl 3-CN, 4-F 160 5-chloropyridin-2-yl 3-Br, 4-F 1615-chloropyridin-2-yl 3-Cl, 4-F 162 5-chloropyridin-2-yl 3,4-Cl₂ 1634-chloropyridin-2-yl H 164 4-chloropyridin-2-yl 2-F 1654-chloropyridin-2-yl 3-F 166 4-chloropyridin-2-yl 4-F 1674-chloropyridin-2-yl 3-Cl 168 4-chloropyridin-2-yl 4-Cl 1694-chloropyridin-2-yl 3-Br 170 4-chloropyridin-2-yl 4-Br 1714-chloropyridin-2-yl 3-I 172 4-chloropyridin-2-yl 3-CN 1734-chloropyridin-2-yl 4-CN 174 4-chloropyridin-2-yl 3-NO₂ 1754-chloropyridin-2-yl 3-Me 176 4-chloropyridin-2-yl 4-Me 1774-chloropyridin-2-yl 2,3-F₂ 178 4-chloropyridin-2-yl 2,4-F₂ 1794-chloropyridin-2-yl 2,5-F₂ 180 4-chloropyridin-2-yl 2,6-F₂ 1814-chloropyridin-2-yl 3,4-F₂ 182 4-chloropyridin-2-yl 3,5-F₂ 1834-chloropyridin-2-yl 3,4,5-F₃ 184 4-chloropyridin-2-yl 3-F, 4-Cl 1854-chloropyridin-2-yl 3-F, 4-Br 186 4-chloropyridin-2-yl 3-CN, 4-F 1874-chloropyridin-2-yl 3-Br, 4-F 188 4-chloropyridin-2-yl 3-Cl, 4-F 1894-chloropyridin-2-yl 3,4-Cl₂ 190 3-chloropyridin-2-yl H 1913-chloropyridin-2-yl 2-F 192 3-chloropyridin-2-yl 3-F 1933-chloropyridin-2-yl 4-F 194 3-chloropyridin-2-yl 3-Cl 1953-chloropyridin-2-yl 4-Cl 196 3-chloropyridin-2-yl 3-Br 1973-chloropyridin-2-yl 4-Br 198 3-chloropyridin-2-yl 3-I 1993-chloropyridin-2-yl 3-CN 200 3-chloropyridin-2-yl 4-CN 2013-chloropyridin-2-yl 3-NO₂ 202 3-chloropyridin-2-yl 3-Me 2033-chloropyridin-2-yl 4-Me 204 3-chloropyridin-2-yl 2,3-F₂ 2053-chloropyridin-2-yl 2,4-F₂ 206 3-chloropyridin-2-yl 2,5-F₂ 2073-chloropyridin-2-yl 2,6-F₂ 208 3-chloropyridin-2-yl 3,4-F₂ 2093-chloropyridin-2-yl 3,5-F₂ 210 3-chloropyridin-2-yl 3,4,5-F₃ 2113-chloropyridin-2-yl 3-F, 4-Cl 212 3-chloropyridin-2-yl 3-F, 4-Br 2133-chloropyridin-2-yl 3-CN, 4-F 214 3-chloropyridin-2-yl 3-Br, 4-F 2153-chloropyridin-2-yl 3-Cl, 4-F 216 3-chloropyridin-2-yl 3,4-Cl₂ 2172-fluoropyridin-3-yl H 218 2-fluoropyridin-3-yl 2-F 2192-fluoropyridin-3-yl 3-F 220 2-fluoropyridin-3-yl 4-F 2212-fluoropyridin-3-yl 3-Cl 222 2-fluoropyridin-3-yl 4-Cl 2232-fluoropyridin-3-yl 3-Br 224 2-fluoropyridin-3-yl 4-Br 2252-fluoropyridin-3-yl 3-I 226 2-fluoropyridin-3-yl 3-CN 2272-fluoropyridin-3-yl 4-CN 228 2-fluoropyridin-3-yl 3-NO₂ 2292-fluoropyridin-3-yl 3-Me 230 2-fluoropyridin-3-yl 4-Me 2312-fluoropyridin-3-yl 2,3-F₂ 232 2-fluoropyridin-3-yl 2,4-F₂ 2332-fluoropyridin-3-yl 2,5-F₂ 234 2-fluoropyridin-3-yl 2,6-F₂ 2352-fluoropyridin-3-yl 3,4-F₂ 236 2-fluoropyridin-3-yl 3,5-F₂ 2372-fluoropyridin-3-yl 3,4,5-F₃ 238 2-fluoropyridin-3-yl 3-F, 4-Cl 2392-fluoropyridin-3-yl 3-F, 4-Br 240 2-fluoropyridin-3-yl 3-CN, 4-F 2412-fluoropyridin-3-yl 3-Br, 4-F 242 2-fluoropyridin-3-yl 3-Cl, 4-F 2432-fluoropyridin-3-yl 3,4-Cl₂ 244 6-fluoropyridin-3-yl H 2456-fluoropyridin-3-yl 2-F 246 6-fluoropyridin-3-yl 3-F 2476-fluoropyridin-3-yl 4-F 248 6-fluoropyridin-3-yl 3-Cl 2496-fluoropyridin-3-yl 4-Cl 250 6-fluoropyridin-3-yl 3-Br 2516-fluoropyridin-3-yl 4-Br 252 6-fluoropyridin-3-yl 3-I 2536-fluoropyridin-3-yl 3-CN 254 6-fluoropyridin-3-yl 4-CN 2556-fluoropyridin-3-yl 3-NO₂ 256 6-fluoropyridin-3-yl 3-Me 2576-fluoropyridin-3-yl 4-Me 258 6-fluoropyridin-3-yl 2,3-F₂ 2596-fluoropyridin-3-yl 2,4-F₂ 260 6-fluoropyridin-3-yl 2,5-F₂ 2616-fluoropyridin-3-yl 2,6-F₂ 262 6-fluoropyridin-3-yl 3,4-F₂ 2636-fluoropyridin-3-yl 3,5-F₂ 264 6-fluoropyridin-3-yl 3,4,5-F₃ 2656-fluoropyridin-3-yl 3-F, 4-Cl 266 6-fluoropyridin-3-yl 3-F, 4-Br 2676-fluoropyridin-3-yl 3-CN, 4-F 268 6-fluoropyridin-3-yl 3-Br, 4-F 2696-fluoropyridin-3-yl 3-Cl, 4-F 270 6-fluoropyridin-3-yl 3,4-Cl₂ 2715-fluoropyridin-3-yl H 272 5-fluoropyridin-3-yl 2-F 2735-fluoropyridin-3-yl 3-F 274 5-fluoropyridin-3-yl 4-F 2755-fluoropyridin-3-yl 3-Cl 276 5-fluoropyridin-3-yl 4-Cl 2775-fluoropyridin-3-yl 3-Br 278 5-fluoropyridin-3-yl 4-Br 2795-fluoropyridin-3-yl 3-I 280 5-fluoropyridin-3-yl 3-CN 2815-fluoropyridin-3-yl 4-CN 282 5-fluoropyridin-3-yl 3-NO₂ 2835-fluoropyridin-3-yl 3-Me 284 5-fluoropyridin-3-yl 4-Me 2855-fluoropyridin-3-yl 2,3-F₂ 286 5-fluoropyridin-3-yl 2,4-F₂ 2875-fluoropyridin-3-yl 2,5-F₂ 288 5-fluoropyridin-3-yl 2,6-F₂ 2895-fluoropyridin-3-yl 3,4-F₂ 290 5-fluoropyridin-3-yl 3,5-F₂ 2915-fluoropyridin-3-yl 3,4,5-F₃ 292 5-fluoropyridin-3-yl 3-F, 4-Cl 2935-fluoropyridin-3-yl 3-F, 4-Br 294 5-fluoropyridin-3-yl 3-CN, 4-F 2955-fluoropyridin-3-yl 3-Br, 4-F 296 5-fluoropyridin-3-yl 3-Cl, 4-F 2975-fluoropyridin-3-yl 3,4-Cl₂ 298 4-fluoropyridin-3-yl H 2994-fluoropyridin-3-yl 2-F 300 4-fluoropyridin-3-yl 3-F 3014-fluoropyridin-3-yl 4-F 302 4-fluoropyridin-3-yl 3-Cl 3034-fluoropyridin-3-yl 4-Cl 304 4-fluoropyridin-3-yl 3-Br 3054-fluoropyridin-3-yl 4-Br 306 4-fluoropyridin-3-yl 3-I 3074-fluoropyridin-3-yl 3-CN 308 4-fluoropyridin-3-yl 4-CN 3094-fluoropyridin-3-yl 3-NO₂ 310 4-fluoropyridin-3-yl 3-Me 3114-fluoropyridin-3-yl 4-Me 312 4-fluoropyridin-3-yl 2,3-F₂ 3134-fluoropyridin-3-yl 2,4-F₂ 314 4-fluoropyridin-3-yl 2,5-F₂ 3154-fluoropyridin-3-yl 2,6-F₂ 316 4-fluoropyridin-3-yl 3,4-F₂ 3174-fluoropyridin-3-yl 3,5-F₂ 318 4-fluoropyridin-3-yl 3,4,5-F₃ 3194-fluoropyridin-3-yl 3-F, 4-Cl 320 4-fluoropyridin-3-yl 3-F, 4-Br 3214-fluoropyridin-3-yl 3-CN, 4-F 322 4-fluoropyridin-3-yl 3-Br, 4-F 3234-fluoropyridin-3-yl 3-Cl, 4-F 324 4-fluoropyridin-3-yl 3,4-Cl₂ 3252-chloropyridin-3-yl H 326 2-chloropyridin-3-yl 2-F 3272-chloropyridin-3-yl 3-F 328 2-chloropyridin-3-yl 4-F 3292-chloropyridin-3-yl 3-Cl 330 2-chloropyridin-3-yl 4-Cl 3312-chloropyridin-3-yl 3-Br 332 2-chloropyridin-3-yl 4-Br 3332-chloropyridin-3-yl 3-I 334 2-chloropyridin-3-yl 3-CN 3352-chloropyridin-3-yl 4-CN 336 2-chloropyridin-3-yl 3-NO₂ 3372-chloropyridin-3-yl 3-Me 338 2-chloropyridin-3-yl 4-Me 3392-chloropyridin-3-yl 2,3-F₂ 340 2-chloropyridin-3-yl 2,4-F₂ 3412-chloropyridin-3-yl 2,5-F₂ 342 2-chloropyridin-3-yl 2,6-F₂ 3432-chloropyridin-3-yl 3,4-F₂ 344 2-chloropyridin-3-yl 3,5-F₂ 3452-chloropyridin-3-yl 3,4,5-F₃ 346 2-chloropyridin-3-yl 3-F, 4-Cl 3472-chloropyridin-3-yl 3-F, 4-Br 348 2-chloropyridin-3-yl 3-CN, 4-F 3492-chloropyridin-3-yl 3-Br, 4-F 350 2-chloropyridin-3-yl 3-Cl, 4-F 3512-chloropyridin-3-yl 3,4-Cl₂ 352 6-chloropyridin-3-yl H 3536-chloropyridin-3-yl 2-F 354 6-chloropyridin-3-yl 3-F 3556-chloropyridin-3-yl 4-F 356 6-chloropyridin-3-yl 3-Cl 3576-chloropyridin-3-yl 4-Cl 358 6-chloropyridin-3-yl 3-Br 3596-chloropyridin-3-yl 4-Br 360 6-chloropyridin-3-yl 3-I 3616-chloropyridin-3-yl 3-CN 362 6-chloropyridin-3-yl 4-CN 3636-chloropyridin-3-yl 3-NO₂ 364 6-chloropyridin-3-yl 3-Me 3656-chloropyridin-3-yl 4-Me 366 6-chloropyridin-3-yl 2,3-F₂ 3676-chloropyridin-3-yl 2,4-F₂ 368 6-chloropyridin-3-yl 2,5-F₂ 3696-chloropyridin-3-yl 2,6-F₂ 370 6-chloropyridin-3-yl 3,4-F₂ 3716-chloropyridin-3-yl 3,5-F₂ 372 6-chloropyridin-3-yl 3,4,5-F₃ 3736-chloropyridin-3-yl 3-F, 4-Cl 374 6-chloropyridin-3-yl 3-F, 4-Br 3756-chloropyridin-3-yl 3-CN, 4-F 376 6-chloropyridin-3-yl 3-Br, 4-F 3776-chloropyridin-3-yl 3-Cl, 4-F 378 6-chloropyridin-3-yl 3,4-Cl₂ 3795-chloropyridin-3-yl H 380 5-chloropyridin-3-yl 2-F 3815-chloropyridin-3-yl 3-F 382 5-chloropyridin-3-yl 4-F 3835-chloropyridin-3-yl 3-Cl 384 5-chloropyridin-3-yl 4-Cl 3855-chloropyridin-3-yl 3-Br 386 5-chloropyridin-3-yl 4-Br 3875-chloropyridin-3-yl 3-I 388 5-chloropyridin-3-yl 3-CN 3895-chloropyridin-3-yl 4-CN 390 5-chloropyridin-3-yl 3-NO₂ 3915-chloropyridin-3-yl 3-Me 392 5-chloropyridin-3-yl 4-Me 3935-chloropyridin-3-yl 2,3-F₂ 394 5-chloropyridin-3-yl 2,4-F₂ 3955-chloropyridin-3-yl 2,5-F₂ 396 5-chloropyridin-3-yl 2,6-F₂ 3975-chloropyridin-3-yl 3,4-F₂ 398 5-chloropyridin-3-yl 3,5-F₂ 3995-chloropyridin-3-yl 3,4,5-F₃ 400 5-chloropyridin-3-yl 3-F, 4-Cl 4015-chloropyridin-3-yl 3-F, 4-Br 402 5-chloropyridin-3-yl 3-CN, 4-F 4035-chloropyridin-3-yl 3-Br, 4-F 404 5-chloropyridin-3-yl 3-Cl, 4-F 4055-chloropyridin-3-yl 3,4-Cl₂ 406 4-chloropyridin-3-yl H 4074-chloropyridin-3-yl 2-F 408 4-chloropyridin-3-yl 3-F 4094-chloropyridin-3-yl 4-F 410 4-chloropyridin-3-yl 3-Cl 4114-chloropyridin-3-yl 4-Cl 412 4-chloropyridin-3-yl 3-Br 4134-chloropyridin-3-yl 4-Br 414 4-chloropyridin-3-yl 3-I 4154-chloropyridin-3-yl 3-CN 416 4-chloropyridin-3-yl 4-CN 4174-chloropyridin-3-yl 3-NO₂ 418 4-chloropyridin-3-yl 3-Me 4194-chloropyridin-3-yl 4-Me 420 4-chloropyridin-3-yl 2,3-F₂ 4214-chloropyridin-3-yl 2,4-F₂ 422 4-chloropyridin-3-yl 2,5-F₂ 4234-chloropyridin-3-yl 2,6-F₂ 424 4-chloropyridin-3-yl 3,4-F₂ 4254-chloropyridin-3-yl 3,5-F₂ 426 4-chloropyridin-3-yl 3,4,5-F₃ 4274-chloropyridin-3-yl 3-F, 4-Cl 428 4-chloropyridin-3-yl 3-F, 4-Br 4294-chloropyridin-3-yl 3-CN, 4-F 430 4-chloropyridin-3-yl 3-Br, 4-F 4314-chloropyridin-3-yl 3-Cl, 4-F 432 4-chloropyridin-3-yl 3,4-Cl₂ 4333-fluoropyridin-4-yl H 434 3-fluoropyridin-4-yl 2-F 4353-fluoropyridin-4-yl 3-F 436 3-fluoropyridin-4-yl 4-F 4373-fluoropyridin-4-yl 3-Cl 438 3-fluoropyridin-4-yl 4-Cl 4393-fluoropyridin-4-yl 3-Br 440 3-fluoropyridin-4-yl 4-Br 4413-fluoropyridin-4-yl 3-I 442 3-fluoropyridin-4-yl 3-CN 4433-fluoropyridin-4-yl 4-CN 444 3-fluoropyridin-4-yl 3-NO₂ 4453-fluoropyridin-4-yl 3-Me 446 3-fluoropyridin-4-yl 4-Me 4473-fluoropyridin-4-yl 2,3-F₂ 448 3-fluoropyridin-4-yl 2,4-F₂ 4493-fluoropyridin-4-yl 2,5-F₂ 450 3-fluoropyridin-4-yl 2,6-F₂ 4513-fluoropyridin-4-yl 3,4-F₂ 452 3-fluoropyridin-4-yl 3,5-F₂ 4533-fluoropyridin-4-yl 3,4,5-F₃ 454 3-fluoropyridin-4-yl 3-F, 4-Cl 4553-fluoropyridin-4-yl 3-F, 4-Br 456 3-fluoropyridin-4-yl 3-CN, 4-F 4573-fluoropyridin-4-yl 3-Br, 4-F 458 3-fluoropyridin-4-yl 3-Cl, 4-F 4593-fluoropyridin-4-yl 3,4-Cl₂ 460 2-fluoropyridin-4-yl H 4612-fluoropyridin-4-yl 2-F 462 2-fluoropyridin-4-yl 3-F 4632-fluoropyridin-4-yl 4-F 464 2-fluoropyridin-4-yl 3-Cl 4652-fluoropyridin-4-yl 4-Cl 466 2-fluoropyridin-4-yl 3-Br 4672-fluoropyridin-4-yl 4-Br 468 2-fluoropyridin-4-yl 3-I 4692-fluoropyridin-4-yl 3-CN 470 2-fluoropyridin-4-yl 4-CN 4712-fluoropyridin-4-yl 3-NO₂ 472 2-fluoropyridin-4-yl 3-Me 4732-fluoropyridin-4-yl 4-Me 474 2-fluoropyridin-4-yl 2,3-F₂ 4752-fluoropyridin-4-yl 2,4-F₂ 476 2-fluoropyridin-4-yl 2,5-F₂ 4772-fluoropyridin-4-yl 2,6-F₂ 478 2-fluoropyridin-4-yl 3,4-F₂ 4792-fluoropyridin-4-yl 3,5-F₂ 480 2-fluoropyridin-4-yl 3,4,5-F₃ 4812-fluoropyridin-4-yl 3-F, 4-Cl 482 2-fluoropyridin-4-yl 3-F, 4-Br 4832-fluoropyridin-4-yl 3-CN, 4-F 484 2-fluoropyridin-4-yl 3-Br, 4-F 4852-fluoropyridin-4-yl 3-Cl, 4-F 486 2-fluoropyridin-4-yl 3,4-Cl₂ 4873-chloropyridin-4-yl H 488 3-chloropyridin-4-yl 2-F 4893-chloropyridin-4-yl 3-F 490 3-chloropyridin-4-yl 4-F 4913-chloropyridin-4-yl 3-Cl 492 3-chloropyridin-4-yl 4-Cl 4933-chloropyridin-4-yl 3-Br 494 3-chloropyridin-4-yl 4-Br 4953-chloropyridin-4-yl 3-I 496 3-chloropyridin-4-yl 3-CN 4973-chloropyridin-4-yl 4-CN 498 3-chloropyridin-4-yl 3-NO₂ 4993-chloropyridin-4-yl 3-Me 500 3-chloropyridin-4-yl 4-Me 5013-chloropyridin-4-yl 2,3-F₂ 502 3-chloropyridin-4-yl 2,4-F₂ 5033-chloropyridin-4-yl 2,5-F₂ 504 3-chloropyridin-4-yl 2,6-F₂ 5053-chloropyridin-4-yl 3,4-F₂ 506 3-chloropyridin-4-yl 3,5-F₂ 5073-chloropyridin-4-yl 3,4,5-F₃ 508 3-chloropyridin-4-yl 3-F, 4-Cl 5093-chloropyridin-4-yl 3-F, 4-Br 510 3-chloropyridin-4-yl 3-CN, 4-F 5113-chloropyridin-4-yl 3-Br, 4-F 512 3-chloropyridin-4-yl 3-Cl, 4-F 5133-chloropyridin-4-yl 3,4-Cl₂ 514 2-chloropyridin-4-yl H 5152-chloropyridin-4-yl 2-F 516 2-chloropyridin-4-yl 3-F 5172-chloropyridin-4-yl 4-F 518 2-chloropyridin-4-yl 3-Cl 5192-chloropyridin-4-yl 4-Cl 520 2-chloropyridin-4-yl 3-Br 5212-chloropyridin-4-yl 4-Br 522 2-chloropyridin-4-yl 3-I 5232-chloropyridin-4-yl 3-CN 524 2-chloropyridin-4-yl 4-CN 5252-chloropyridin-4-yl 3-NO₂ 526 2-chloropyridin-4-yl 3-Me 5272-chloropyridin-4-yl 4-Me 528 2-chloropyridin-4-yl 2,3-F₂ 5292-chloropyridin-4-yl 2,4-F₂ 530 2-chloropyridin-4-yl 2,5-F₂ 5312-chloropyridin-4-yl 2,6-F₂ 532 2-chloropyridin-4-yl 3,4-F₂ 5332-chloropyridin-4-yl 3,5-F₂ 534 2-chloropyridin-4-yl 3,4,5-F₃ 5352-chloropyridin-4-yl 3-F, 4-Cl 536 2-chloropyridin-4-yl 3-F, 4-Br 5372-chloropyridin-4-yl 3-CN, 4-F 538 2-chloropyridin-4-yl 3-Br, 4-F 5392-chloropyridin-4-yl 3-Cl, 4-F 540 2-chloropyridin-4-yl 3,4-Cl₂ 5412,3-difluoropyridin-4-yl H 542 2,3-difluoropyridin-4-yl 2-F 5432,3-difluoropyridin-4-yl 3-F 544 2,3-difluoropyridin-4-yl 4-F 5452,3-difluoropyridin-4-yl 3-Cl 546 2,3-difluoropyridin-4-yl 4-Cl 5472,3-difluoropyridin-4-yl 3-Br 548 2,3-difluoropyridin-4-yl 4-Br 5492,3-difluoropyridin-4-yl 3-I 550 2,3-difluoropyridin-4-yl 3-CN 5512,3-difluoropyridin-4-yl 4-CN 552 2,3-difluoropyridin-4-yl 3-NO₂ 5532,3-difluoropyridin-4-yl 3-Me 554 2,3-difluoropyridin-4-yl 4-Me 5552,3-difluoropyridin-4-yl 2,3-F₂ 556 2,3-difluoropyridin-4-yl 2,4-F₂ 5572,3-difluoropyridin-4-yl 2,5-F₂ 558 2,3-difluoropyridin-4-yl 2,6-F₂ 5592,3-difluoropyridin-4-yl 3,4-F₂ 560 2,3-difluoropyridin-4-yl 3,5-F₂ 5612,3-difluoropyridin-4-yl 3,4,5-F₃ 562 2,3-difluoropyridin-4-yl 3-F, 4-Cl563 2,3-difluoropyridin-4-yl 3-F, 4-Br 564 2,3-difluoropyridin-4-yl3-CN, 4-F 565 2,3-difluoropyridin-4-yl 3-Br, 4-F 5662,3-difluoropyridin-4-yl 3-Cl, 4-F 567 2,3-difluoropyridin-4-yl 3,4-Cl₂568 2,5-difluoropyridin-4-yl H 569 2,5-difluoropyridin-4-yl 2-F 5702,5-difluoropyridin-4-yl 3-F 571 2,5-difluoropyridin-4-yl 4-F 5722,5-difluoropyridin-4-yl 3-Cl 573 2,5-difluoropyridin-4-yl 4-Cl 5742,5-difluoropyridin-4-yl 3-Br 575 2,5-difluoropyridin-4-yl 4-Br 5762,5-difluoropyridin-4-yl 3-I 577 2,5-difluoropyridin-4-yl 3-CN 5782,5-difluoropyridin-4-yl 4-CN 579 2,5-difluoropyridin-4-yl 3-NO₂ 5802,5-difluoropyridin-4-yl 3-Me 581 2,5-difluoropyridin-4-yl 4-Me 5822,5-difluoropyridin-4-yl 2,3-F₂ 583 2,5-difluoropyridin-4-yl 2,4-F₂ 5842,5-difluoropyridin-4-yl 2,5-F₂ 585 2,5-difluoropyridin-4-yl 2,6-F₂ 5862,5-difluoropyridin-4-yl 3,4-F₂ 587 2,5-difluoropyridin-4-yl 3,5-F₂ 5882,5-difluoropyridin-4-yl 3,4,5-F₃ 589 2,5-difluoropyridin-4-yl 3-F, 4-Cl590 2,5-difluoropyridin-4-yl 3-F, 4-Br 591 2,5-difluoropyridin-4-yl3-CN, 4-F 592 2,5-difluoropyridin-4-yl 3-Br, 4-F 5932,5-difluoropyridin-4-yl 3-Cl, 4-F 594 2,5-difluoropyridin-4-yl 3,4-Cl₂595 3,5-difluoropyridin-4-yl H 596 3,5-difluoropyridin-4-yl 2-F 5973,5-difluoropyridin-4-yl 3-F 598 3,5-difluoropyridin-4-yl 4-F 5993,5-difluoropyridin-4-yl 3-Cl 600 3,5-difluoropyridin-4-yl 4-Cl 6013,5-difluoropyridin-4-yl 3-Br 602 3,5-difluoropyridin-4-yl 4-Br 6033,5-difluoropyridin-4-yl 3-I 604 3,5-difluoropyridin-4-yl 3-CN 6053,5-difluoropyridin-4-yl 4-CN 606 3,5-difluoropyridin-4-yl 3-NO₂ 6073,5-difluoropyridin-4-yl 3-Me 608 3,5-difluoropyridin-4-yl 4-Me 6093,5-difluoropyridin-4-yl 2,3-F₂ 610 3,5-difluoropyridin-4-yl 2,4-F₂ 6113,5-difluoropyridin-4-yl 2,5-F₂ 612 3,5-difluoropyridin-4-yl 2,6-F₂ 6133,5-difluoropyridin-4-yl 3,4-F₂ 614 3,5-difluoropyridin-4-yl 3,5-F₂ 6153,5-difluoropyridin-4-yl 3,4,5-F₃ 616 3,5-difluoropyridin-4-yl 3-F, 4-Cl617 3,5-difluoropyridin-4-yl 3-F, 4-Br 618 3,5-difluoropyridin-4-yl3-CN, 4-F 619 3,5-difluoropyridin-4-yl 3-Br, 4-F 6203,5-difluoropyridin-4-yl 3-Cl, 4-F 621 3,5-difluoropyridin-4-yl 3,4-Cl₂622 2,4-difluoropyridin-3-yl H 623 2,4-difluoropyridin-3-yl 2-F 6242,4-difluoropyridin-3-yl 3-F 625 2,4-difluoropyridin-3-yl 4-F 6262,4-difluoropyridin-3-yl 3-Cl 627 2,4-difluoropyridin-3-yl 4-Cl 6282,4-difluoropyridin-3-yl 3-Br 629 2,4-difluoropyridin-3-yl 4-Br 6302,4-difluoropyridin-3-yl 3-I 631 2,4-difluoropyridin-3-yl 3-CN 6322,4-difluoropyridin-3-yl 4-CN 633 2,4-difluoropyridin-3-yl 3-NO₂ 6342,4-difluoropyridin-3-yl 3-Me 635 2,4-difluoropyridin-3-yl 4-Me 6362,4-difluoropyridin-3-yl 2,3-F₂ 637 2,4-difluoropyridin-3-yl 2,4-F₂ 6382,4-difluoropyridin-3-yl 2,5-F₂ 639 2,4-difluoropyridin-3-yl 2,6-F₂ 6402,4-difluoropyridin-3-yl 3,4-F₂ 641 2,4-difluoropyridin-3-yl 3,5-F₂ 6422,4-difluoropyridin-3-yl 3,4,5-F₃ 643 2,4-difluoropyridin-3-yl 3-F, 4-Cl644 2,4-difluoropyridin-3-yl 3-F, 4-Br 645 2,4-difluoropyridin-3-yl3-CN, 4-F 646 2,4-difluoropyridin-3-yl 3-Br, 4-F 6472,4-difluoropyridin-3-yl 3-Cl, 4-F 648 2,4-difluoropyridin-3-yl 3,4-Cl₂649 2,5-difluoropyridin-3-yl H 650 2,5-difluoropyridin-3-yl 2-F 6512,5-difluoropyridin-3-yl 3-F 652 2,5-difluoropyridin-3-yl 4-F 6532,5-difluoropyridin-3-yl 3-Cl 654 2,5-difluoropyridin-3-yl 4-Cl 6552,5-difluoropyridin-3-yl 3-Br 656 2,5-difluoropyridin-3-yl 4-Br 6572,5-difluoropyridin-3-yl 3-I 658 2,5-difluoropyridin-3-yl 3-CN 6592,5-difluoropyridin-3-yl 4-CN 660 2,5-difluoropyridin-3-yl 3-NO₂ 6612,5-difluoropyridin-3-yl 3-Me 662 2,5-difluoropyridin-3-yl 4-Me 6632,5-difluoropyridin-3-yl 2,3-F₂ 664 2,5-difluoropyridin-3-yl 2,4-F₂ 6652,5-difluoropyridin-3-yl 2,5-F₂ 666 2,5-difluoropyridin-3-yl 2,6-F₂ 6672,5-difluoropyridin-3-yl 3,4-F₂ 668 2,5-difluoropyridin-3-yl 3,5-F₂ 6692,5-difluoropyridin-3-yl 3,4,5-F₃ 670 2,5-difluoropyridin-3-yl 3-F, 4-Cl671 2,5-difluoropyridin-3-yl 3-F, 4-Br 672 2,5-difluoropyridin-3-yl3-CN, 4-F 673 2,5-difluoropyridin-3-yl 3-Br, 4-F 6742,5-difluoropyridin-3-yl 3-Cl, 4-F 675 2,5-difluoropyridin-3-yl 3,4-Cl₂676 2,6-difluoropyridin-3-yl H 677 2,6-difluoropyridin-3-yl 2-F 6782,6-difluoropyridin-3-yl 3-F 679 2,6-difluoropyridin-3-yl 4-F 6802,6-difluoropyridin-3-yl 3-Cl 681 2,6-difluoropyridin-3-yl 4-Cl 6822,6-difluoropyridin-3-yl 3-Br 683 2,6-difluoropyridin-3-yl 4-Br 6842,6-difluoropyridin-3-yl 3-I 685 2,6-difluoropyridin-3-yl 3-CN 6862,6-difluoropyridin-3-yl 4-CN 687 2,6-difluoropyridin-3-yl 3-NO₂ 6882,6-difluoropyridin-3-yl 3-Me 689 2,6-difluoropyridin-3-yl 4-Me 6902,6-difluoropyridin-3-yl 2,3-F₂ 691 2,6-difluoropyridin-3-yl 2,4-F₂ 6922,6-difluoropyridin-3-yl 2,5-F₂ 693 2,6-difluoropyridin-3-yl 2,6-F₂ 6942,6-difluoropyridin-3-yl 3,4-F₂ 695 2,6-difluoropyridin-3-yl 3,5-F₂ 6962,6-difluoropyridin-3-yl 3,4,5-F₃ 697 2,6-difluoropyridin-3-yl 3-F, 4-Cl698 2,6-difluoropyridin-3-yl 3-F, 4-Br 699 2,6-difluoropyridin-3-yl3-CN, 4-F 700 2,6-difluoropyridin-3-yl 3-Br, 4-F 7012,6-difluoropyridin-3-yl 3-Cl, 4-F 702 2,6-difluoropyridin-3-yl 3,4-Cl₂703 5,6-difluoropyridin-3-yl H 704 5,6-difluoropyridin-3-yl 2-F 7055,6-difluoropyridin-3-yl 3-F 706 5,6-difluoropyridin-3-yl 4-F 7075,6-difluoropyridin-3-yl 3-Cl 708 5,6-difluoropyridin-3-yl 4-Cl 7095,6-difluoropyridin-3-yl 3-Br 710 5,6-difluoropyridin-3-yl 4-Br 7115,6-difluoropyridin-3-yl 3-I 712 5,6-difluoropyridin-3-yl 3-CN 7135,6-difluoropyridin-3-yl 4-CN 714 5,6-difluoropyridin-3-yl 3-NO₂ 7155,6-difluoropyridin-3-yl 3-Me 716 5,6-difluoropyridin-3-yl 4-Me 7175,6-difluoropyridin-3-yl 2,3-F₂ 718 5,6-difluoropyridin-3-yl 2,4-F₂ 7195,6-difluoropyridin-3-yl 2,5-F₂ 720 5,6-difluoropyridin-3-yl 2,6-F₂ 7215,6-difluoropyridin-3-yl 3,4-F₂ 722 5,6-difluoropyridin-3-yl 3,5-F₂ 7235,6-difluoropyridin-3-yl 3,4,5-F₃ 724 5,6-difluoropyridin-3-yl 3-F, 4-Cl725 5,6-difluoropyridin-3-yl 3-F, 4-Br 726 5,6-difluoropyridin-3-yl3-CN, 4-F 727 5,6-difluoropyridin-3-yl 3-Br, 4-F 7285,6-difluoropyridin-3-yl 3-Cl, 4-F 729 5,6-difluoropyridin-3-yl 3,4-Cl₂730 4,5-difluoropyridin-3-yl H 731 4,5-difluoropyridin-3-yl 2-F 7324,5-difluoropyridin-3-yl 3-F 733 4,5-difluoropyridin-3-yl 4-F 7344,5-difluoropyridin-3-yl 3-Cl 735 4,5-difluoropyridin-3-yl 4-Cl 7364,5-difluoropyridin-3-yl 3-Br 737 4,5-difluoropyridin-3-yl 4-Br 7384,5-difluoropyridin-3-yl 3-I 739 4,5-difluoropyridin-3-yl 3-CN 7404,5-difluoropyridin-3-yl 4-CN 741 4,5-difluoropyridin-3-yl 3-NO₂ 7424,5-difluoropyridin-3-yl 3-Me 743 4,5-difluoropyridin-3-yl 4-Me 7444,5-difluoropyridin-3-yl 2,3-F₂ 745 4,5-difluoropyridin-3-yl 2,4-F₂ 7464,5-difluoropyridin-3-yl 2,5-F₂ 747 4,5-difluoropyridin-3-yl 2,6-F₂ 7484,5-difluoropyridin-3-yl 3,4-F₂ 749 4,5-difluoropyridin-3-yl 3,5-F₂ 7504,5-difluoropyridin-3-yl 3,4,5-F₃ 751 4,5-difluoropyridin-3-yl 3-F, 4-Cl752 4,5-difluoropyridin-3-yl 3-F, 4-Br 753 4,5-difluoropyridin-3-yl3-CN, 4-F 754 4,5-difluoropyridin-3-yl 3-Br, 4-F 7554,5-difluoropyridin-3-yl 3-Cl, 4-F 756 4,5-difluoropyridin-3-yl 3,4-Cl₂757 4,6-difluoropyridin-3-yl H 758 4,6-difluoropyridin-3-yl 2-F 7594,6-difluoropyridin-3-yl 3-F 760 4,6-difluoropyridin-3-yl 4-F 7614,6-difluoropyridin-3-yl 3-Cl 762 4,6-difluoropyridin-3-yl 4-Cl 7634,6-difluoropyridin-3-yl 3-Br 764 4,6-difluoropyridin-3-yl 4-Br 7654,6-difluoropyridin-3-yl 3-I 766 4,6-difluoropyridin-3-yl 3-CN 7674,6-difluoropyridin-3-yl 4-CN 768 4,6-difluoropyridin-3-yl 3-NO₂ 7694,6-difluoropyridin-3-yl 3-Me 770 4,6-difluoropyridin-3-yl 4-Me 7714,6-difluoropyridin-3-yl 2,3-F₂ 772 4,6-difluoropyridin-3-yl 2,4-F₂ 7734,6-difluoropyridin-3-yl 2,5-F₂ 774 4,6-difluoropyridin-3-yl 2,6-F₂ 7754,6-difluoropyridin-3-yl 3,4-F₂ 776 4,6-difluoropyridin-3-yl 3,5-F₂ 7774,6-difluoropyridin-3-yl 3,4,5-F₃ 778 4,6-difluoropyridin-3-yl 3-F, 4-Cl779 4,6-difluoropyridin-3-yl 3-F, 4-Br 780 4,6-difluoropyridin-3-yl3-CN, 4-F 781 4,6-difluoropyridin-3-yl 3-Br, 4-F 7824,6-difluoropyridin-3-yl 3-Cl, 4-F 783 4,6-difluoropyridin-3-yl 3,4-Cl₂784 3,5-difluoropyridin-2-yl H 785 3,5-difluoropyridin-2-yl 2-F 7863,5-difluoropyridin-2-yl 3-F 787 3,5-difluoropyridin-2-yl 4-F 7883,5-difluoropyridin-2-yl 3-Cl 789 3,5-difluoropyridin-2-yl 4-Cl 7903,5-difluoropyridin-2-yl 3-Br 791 3,5-difluoropyridin-2-yl 4-Br 7923,5-difluoropyridin-2-yl 3-I 793 3,5-difluoropyridin-2-yl 3-CN 7943,5-difluoropyridin-2-yl 4-CN 795 3,5-difluoropyridin-2-yl 3-NO₂ 7963,5-difluoropyridin-2-yl 3-Me 797 3,5-difluoropyridin-2-yl 4-Me 7983,5-difluoropyridin-2-yl 2,3-F₂ 799 3,5-difluoropyridin-2-yl 2,4-F₂ 8003,5-difluoropyridin-2-yl 2,5-F₂ 801 3,5-difluoropyridin-2-yl 2,6-F₂ 8023,5-difluoropyridin-2-yl 3,4-F₂ 803 3,5-difluoropyridin-2-yl 3,5-F₂ 8043,5-difluoropyridin-2-yl 3,4,5-F₃ 805 3,5-difluoropyridin-2-yl 3-F, 4-Cl806 3,5-difluoropyridin-2-yl 3-F, 4-Br 807 3,5-difluoropyridin-2-yl3-CN, 4-F 808 3,5-difluoropyridin-2-yl 3-Br, 4-F 8093,5-difluoropyridin-2-yl 3-Cl, 4-F 810 3,5-difluoropyridin-2-yl 3,4-Cl₂811 3,6-difluoropyridin-2-yl H 812 3,6-difluoropyridin-2-yl 2-F 8133,6-difluoropyridin-2-yl 3-F 814 3,6-difluoropyridin-2-yl 4-F 8153,6-difluoropyridin-2-yl 3-Cl 816 3,6-difluoropyridin-2-yl 4-Cl 8173,6-difluoropyridin-2-yl 3-Br 818 3,6-difluoropyridin-2-yl 4-Br 8193,6-difluoropyridin-2-yl 3-I 820 3,6-difluoropyridin-2-yl 3-CN 8213,6-difluoropyridin-2-yl 4-CN 822 3,6-difluoropyridin-2-yl 3-NO₂ 8233,6-difluoropyridin-2-yl 3-Me 824 3,6-difluoropyridin-2-yl 4-Me 8253,6-difluoropyridin-2-yl 2,3-F₂ 826 3,6-difluoropyridin-2-yl 2,4-F₂ 8273,6-difluoropyridin-2-yl 2,5-F₂ 828 3,6-difluoropyridin-2-yl 2,6-F₂ 8293,6-difluoropyridin-2-yl 3,4-F₂ 830 3,6-difluoropyridin-2-yl 3,5-F₂ 8313,6-difluoropyridin-2-yl 3,4,5-F₃ 832 3,6-difluoropyridin-2-yl 3-F, 4-Cl833 3,6-difluoropyridin-2-yl 3-F, 4-Br 834 3,6-difluoropyridin-2-yl3-CN, 4-F 835 3,6-difluoropyridin-2-yl 3-Br, 4-F 8363,6-difluoropyridin-2-yl 3-Cl, 4-F 837 3,6-difluoropyridin-2-yl 3,4-Cl₂838 4,6-difluoropyridin-2-yl H 839 4,6-difluoropyridin-2-yl 2-F 8404,6-difluoropyridin-2-yl 3-F 841 4,6-difluoropyridin-2-yl 4-F 8424,6-difluoropyridin-2-yl 3-Cl 843 4,6-difluoropyridin-2-yl 4-Cl 8444,6-difluoropyridin-2-yl 3-Br 845 4,6-difluoropyridin-2-yl 4-Br 8464,6-difluoropyridin-2-yl 3-I 847 4,6-difluoropyridin-2-yl 3-CN 8484,6-difluoropyridin-2-yl 4-CN 849 4,6-difluoropyridin-2-yl 3-NO₂ 8504,6-difluoropyridin-2-yl 3-Me 851 4,6-difluoropyridin-2-yl 4-Me 8524,6-difluoropyridin-2-yl 2,3-F₂ 853 4,6-difluoropyridin-2-yl 2,4-F₂ 8544,6-difluoropyridin-2-yl 2,5-F₂ 855 4,6-difluoropyridin-2-yl 2,6-F₂ 8564,6-difluoropyridin-2-yl 3,4-F₂ 857 4,6-difluoropyridin-2-yl 3,5-F₂ 8584,6-difluoropyridin-2-yl 3,4,5-F₃ 859 4,6-difluoropyridin-2-yl 3-F, 4-Cl860 4,6-difluoropyridin-2-yl 3-F, 4-Br 861 4,6-difluoropyridin-2-yl3-CN, 4-F 862 4,6-difluoropyridin-2-yl 3-Br, 4-F 8634,6-difluoropyridin-2-yl 3-Cl, 4-F 864 4,6-difluoropyridin-2-yl 3,4-Cl₂865 5,6-difluoropyridin-2-yl H 866 5,6-difluoropyridin-2-yl 2-F 8675,6-difluoropyridin-2-yl 3-F 868 5,6-difluoropyridin-2-yl 4-F 8695,6-difluoropyridin-2-yl 3-Cl 870 5,6-difluoropyridin-2-yl 4-Cl 8715,6-difluoropyridin-2-yl 3-Br 872 5,6-difluoropyridin-2-yl 4-Br 8735,6-difluoropyridin-2-yl 3-I 874 5,6-difluoropyridin-2-yl 3-CN 8755,6-difluoropyridin-2-yl 4-CN 876 5,6-difluoropyridin-2-yl 3-NO₂ 8775,6-difluoropyridin-2-yl 3-Me 878 5,6-difluoropyridin-2-yl 4-Me 8795,6-difluoropyridin-2-yl 2,3-F₂ 880 5,6-difluoropyridin-2-yl 2,4-F₂ 8815,6-difluoropyridin-2-yl 2,5-F₂ 882 5,6-difluoropyridin-2-yl 2,6-F₂ 8835,6-difluoropyridin-2-yl 3,4-F₂ 884 5,6-difluoropyridin-2-yl 3,5-F₂ 8855,6-difluoropyridin-2-yl 3,4,5-F₃ 886 5,6-difluoropyridin-2-yl 3-F, 4-Cl887 5,6-difluoropyridin-2-yl 3-F, 4-Br 888 5,6-difluoropyridin-2-yl3-CN, 4-F 889 5,6-difluoropyridin-2-yl 3-Br, 4-F 8905,6-difluoropyridin-2-yl 3-Cl, 4-F 891 5,6-difluoropyridin-2-yl 3,4-Cl₂892 4,5-difluoropyridin-2-yl H 893 4,5-difluoropyridin-2-yl 2-F 8944,5-difluoropyridin-2-yl 3-F 895 4,5-difluoropyridin-2-yl 4-F 8964,5-difluoropyridin-2-yl 3-Cl 897 4,5-difluoropyridin-2-yl 4-Cl 8984,5-difluoropyridin-2-yl 3-Br 899 4,5-difluoropyridin-2-yl 4-Br 9004,5-difluoropyridin-2-yl 3-I 901 4,5-difluoropyridin-2-yl 3-CN 9024,5-difluoropyridin-2-yl 4-CN 903 4,5-difluoropyridin-2-yl 3-NO₂ 9044,5-difluoropyridin-2-yl 3-Me 905 4,5-difluoropyridin-2-yl 4-Me 9064,5-difluoropyridin-2-yl 2,3-F₂ 907 4,5-difluoropyridin-2-yl 2,4-F₂ 9084,5-difluoropyridin-2-yl 2,5-F₂ 909 4,5-difluoropyridin-2-yl 2,6-F₂ 9104,5-difluoropyridin-2-yl 3,4-F₂ 911 4,5-difluoropyridin-2-yl 3,5-F₂ 9124,5-difluoropyridin-2-yl 3,4,5-F₃ 913 4,5-difluoropyridin-2-yl 3-F, 4-Cl914 4,5-difluoropyridin-2-yl 3-F, 4-Br 915 4,5-difluoropyridin-2-yl3-CN, 4-F 916 4,5-difluoropyridin-2-yl 3-Br, 4-F 9174,5-difluoropyridin-2-yl 3-Cl, 4-F 918 4,5-difluoropyridin-2-yl 3,4-Cl₂919 6-methoxypyridin-2-yl H 920 6-methoxypyridin-2-yl 2-F 9216-methoxypyridin-2-yl 3-F 922 6-methoxypyridin-2-yl 4-F 9236-methoxypyridin-2-yl 3-Cl 924 6-methoxypyridin-2-yl 4-Cl 9256-methoxypyridin-2-yl 3-Br 926 6-methoxypyridin-2-yl 4-Br 9276-methoxypyridin-2-yl 3-I 928 6-methoxypyridin-2-yl 3-CN 9296-methoxypyridin-2-yl 4-CN 930 6-methoxypyridin-2-yl 3-NO₂ 9316-methoxypyridin-2-yl 3-Me 932 6-methoxypyridin-2-yl 4-Me 9336-methoxypyridin-2-yl 2,3-F₂ 934 6-methoxypyridin-2-yl 2,4-F₂ 9356-methoxypyridin-2-yl 2,5-F₂ 936 6-methoxypyridin-2-yl 2,6-F₂ 9376-methoxypyridin-2-yl 3,4-F₂ 938 6-methoxypyridin-2-yl 3,5-F₂ 9396-methoxypyridin-2-yl 3,4,5-F₃ 940 6-methoxypyridin-2-yl 3-F, 4-Cl 9416-methoxypyridin-2-yl 3-F, 4-Br 942 6-methoxypyridin-2-yl 3-CN, 4-F 9436-methoxypyridin-2-yl 3-Br, 4-F 944 6-methoxypyridin-2-yl 3-Cl, 4-F 9456-methoxypyridin-2-yl 3,4-Cl₂ 946 5-methoxypyridin-2-yl H 9475-methoxypyridin-2-yl 2-F 948 5-methoxypyridin-2-yl 3-F 9495-methoxypyridin-2-yl 4-F 950 5-methoxypyridin-2-yl 3-Cl 9515-methoxypyridin-2-yl 4-Cl 952 5-methoxypyridin-2-yl 3-Br 9535-methoxypyridin-2-yl 4-Br 954 5-methoxypyridin-2-yl 3-I 9555-methoxypyridin-2-yl 3-CN 956 5-methoxypyridin-2-yl 4-CN 9575-methoxypyridin-2-yl 3-NO₂ 958 5-methoxypyridin-2-yl 3-Me 9595-methoxypyridin-2-yl 4-Me 960 5-methoxypyridin-2-yl 2,3-F₂ 9615-methoxypyridin-2-yl 2,4-F₂ 962 5-methoxypyridin-2-yl 2,5-F₂ 9635-methoxypyridin-2-yl 2,6-F₂ 964 5-methoxypyridin-2-yl 3,4-F₂ 9655-methoxypyridin-2-yl 3,5-F₂ 966 5-methoxypyridin-2-yl 3,4,5-F₃ 9675-methoxypyridin-2-yl 3-F, 4-Cl 968 5-methoxypyridin-2-yl 3-F, 4-Br 9695-methoxypyridin-2-yl 3-CN, 4-F 970 5-methoxypyridin-2-yl 3-Br, 4-F 9715-methoxypyridin-2-yl 3-Cl, 4-F 972 5-methoxypyridin-2-yl 3,4-Cl₂ 9734-methoxypyridin-2-yl H 974 4-methoxypyridin-2-yl 2-F 9754-methoxypyridin-2-yl 3-F 976 4-methoxypyridin-2-yl 4-F 9774-methoxypyridin-2-yl 3-Cl 978 4-methoxypyridin-2-yl 4-Cl 9794-methoxypyridin-2-yl 3-Br 980 4-methoxypyridin-2-yl 4-Br 9814-methoxypyridin-2-yl 3-I 982 4-methoxypyridin-2-yl 3-CN 9834-methoxypyridin-2-yl 4-CN 984 4-methoxypyridin-2-yl 3-NO₂ 9854-methoxypyridin-2-yl 3-Me 986 4-methoxypyridin-2-yl 4-Me 9874-methoxypyridin-2-yl 2,3-F₂ 988 4-methoxypyridin-2-yl 2,4-F₂ 9894-methoxypyridin-2-yl 2,5-F₂ 990 4-methoxypyridin-2-yl 2,6-F₂ 9914-methoxypyridin-2-yl 3,4-F₂ 992 4-methoxypyridin-2-yl 3,5-F₂ 9934-methoxypyridin-2-yl 3,4,5-F₃ 994 4-methoxypyridin-2-yl 3-F, 4-Cl 9954-methoxypyridin-2-yl 3-F, 4-Br 996 4-methoxypyridin-2-yl 3-CN, 4-F 9974-methoxypyridin-2-yl 3-Br, 4-F 998 4-methoxypyridin-2-yl 3-Cl, 4-F 9994-methoxypyridin-2-yl 3,4-Cl₂ 1000 3-methoxypyridin-2-yl H 10013-methoxypyridin-2-yl 2-F 1002 3-methoxypyridin-2-yl 3-F 10033-methoxypyridin-2-yl 4-F 1004 3-methoxypyridin-2-yl 3-Cl 10053-methoxypyridin-2-yl 4-Cl 1006 3-methoxypyridin-2-yl 3-Br 10073-methoxypyridin-2-yl 4-Br 1008 3-methoxypyridin-2-yl 3-I 10093-methoxypyridin-2-yl 3-CN 1010 3-methoxypyridin-2-yl 4-CN 10113-methoxypyridin-2-yl 3-NO₂ 1012 3-methoxypyridin-2-yl 3-Me 10133-methoxypyridin-2-yl 4-Me 1014 3-methoxypyridin-2-yl 2,3-F₂ 10153-methoxypyridin-2-yl 2,4-F₂ 1016 3-methoxypyridin-2-yl 2,5-F₂ 10173-methoxypyridin-2-yl 2,6-F₂ 1018 3-methoxypyridin-2-yl 3,4-F₂ 10193-methoxypyridin-2-yl 3,5-F₂ 1020 3-methoxypyridin-2-yl 3,4,5-F₃ 10213-methoxypyridin-2-yl 3-F, 4-Cl 1022 3-methoxypyridin-2-yl 3-F, 4-Br1023 3-methoxypyridin-2-yl 3-CN, 4-F 1024 3-methoxypyridin-2-yl 3-Br,4-F 1025 3-methoxypyridin-2-yl 3-Cl, 4-F 1026 3-methoxypyridin-2-yl3,4-Cl₂ 1027 4-methoxypyridin-3-yl H 1028 4-methoxypyridin-3-yl 2-F 10294-methoxypyridin-3-yl 3-F 1030 4-methoxypyridin-3-yl 4-F 10314-methoxypyridin-3-yl 3-Cl 1032 4-methoxypyridin-3-yl 4-Cl 10334-methoxypyridin-3-yl 3-Br 1034 4-methoxypyridin-3-yl 4-Br 10354-methoxypyridin-3-yl 3-I 1036 4-methoxypyridin-3-yl 3-CN 10374-methoxypyridin-3-yl 4-CN 1038 4-methoxypyridin-3-yl 3-NO₂ 10394-methoxypyridin-3-yl 3-Me 1040 4-methoxypyridin-3-yl 4-Me 10414-methoxypyridin-3-yl 2,3-F₂ 1042 4-methoxypyridin-3-yl 2,4-F₂ 10434-methoxypyridin-3-yl 2,5-F₂ 1044 4-methoxypyridin-3-yl 2,6-F₂ 10454-methoxypyridin-3-yl 3,4-F₂ 1046 4-methoxypyridin-3-yl 3,5-F₂ 10474-methoxypyridin-3-yl 3,4,5-F₃ 1048 4-methoxypyridin-3-yl 3-F, 4-Cl 10494-methoxypyridin-3-yl 3-F, 4-Br 1050 4-methoxypyridin-3-yl 3-CN, 4-F1051 4-methoxypyridin-3-yl 3-Br, 4-F 1052 4-methoxypyridin-3-yl 3-Cl,4-F 1053 4-methoxypyridin-3-yl 3,4-Cl₂ 1054 5-methoxypyridin-3-yl H 10555-methoxypyridin-3-yl 2-F 1056 5-methoxypyridin-3-yl 3-F 10575-methoxypyridin-3-yl 4-F 1058 5-methoxypyridin-3-yl 3-Cl 10595-methoxypyridin-3-yl 4-Cl 1060 5-methoxypyridin-3-yl 3-Br 10615-methoxypyridin-3-yl 4-Br 1062 5-methoxypyridin-3-yl 3-I 10635-methoxypyridin-3-yl 3-CN 1064 5-methoxypyridin-3-yl 4-CN 10655-methoxypyridin-3-yl 3-NO₂ 1066 5-methoxypyridin-3-yl 3-Me 10675-methoxypyridin-3-yl 4-Me 1068 5-methoxypyridin-3-yl 2,3-F₂ 10695-methoxypyridin-3-yl 2,4-F₂ 1070 5-methoxypyridin-3-yl 2,5-F₂ 10715-methoxypyridin-3-yl 2,6-F₂ 1072 5-methoxypyridin-3-yl 3,4-F₂ 10735-methoxypyridin-3-yl 3,5-F₂ 1074 5-methoxypyridin-3-yl 3,4,5-F₃ 10755-methoxypyridin-3-yl 3-F, 4-Cl 1076 5-methoxypyridin-3-yl 3-F, 4-Br1077 5-methoxypyridin-3-yl 3-CN, 4-F 1078 5-methoxypyridin-3-yl 3-Br,4-F 1079 5-methoxypyridin-3-yl 3-Cl, 4-F 1080 5-methoxypyridin-3-yl3,4-Cl₂ 1081 6-methoxypyridin-3-yl H 1082 6-methoxypyridin-3-yl 2-F 10836-methoxypyridin-3-yl 3-F 1084 6-methoxypyridin-3-yl 4-F 10856-methoxypyridin-3-yl 3-Cl 1086 6-methoxypyridin-3-yl 4-Cl 10876-methoxypyridin-3-yl 3-Br 1088 6-methoxypyridin-3-yl 4-Br 10896-methoxypyridin-3-yl 3-I 1090 6-methoxypyridin-3-yl 3-CN 10916-methoxypyridin-3-yl 4-CN 1092 6-methoxypyridin-3-yl 3-NO₂ 10936-methoxypyridin-3-yl 3-Me 1094 6-methoxypyridin-3-yl 4-Me 10956-methoxypyridin-3-yl 2,3-F₂ 1096 6-methoxypyridin-3-yl 2,4-F₂ 10976-methoxypyridin-3-yl 2,5-F₂ 1098 6-methoxypyridin-3-yl 2,6-F₂ 10996-methoxypyridin-3-yl 3,4-F₂ 1100 6-methoxypyridin-3-yl 3,5-F₂ 11016-methoxypyridin-3-yl 3,4,5-F₃ 1102 6-methoxypyridin-3-yl 3-F, 4-Cl 11036-methoxypyridin-3-yl 3-F, 4-Br 1104 6-methoxypyridin-3-yl 3-CN, 4-F1105 6-methoxypyridin-3-yl 3-Br, 4-F 1106 6-methoxypyridin-3-yl 3-Cl,4-F 1107 6-methoxypyridin-3-yl 3,4-Cl₂ 1108 2-methoxypyridin-3-yl H 11092-methoxypyridin-3-yl 2-F 1110 2-methoxypyridin-3-yl 3-F 11112-methoxypyridin-3-yl 4-F 1112 2-methoxypyridin-3-yl 3-Cl 11132-methoxypyridin-3-yl 4-Cl 1114 2-methoxypyridin-3-yl 3-Br 11152-methoxypyridin-3-yl 4-Br 1116 2-methoxypyridin-3-yl 3-I 11172-methoxypyridin-3-yl 3-CN 1118 2-methoxypyridin-3-yl 4-CN 11192-methoxypyridin-3-yl 3-NO₂ 1120 2-methoxypyridin-3-yl 3-Me 11212-methoxypyridin-3-yl 4-Me 1122 2-methoxypyridin-3-yl 2,3-F₂ 11232-methoxypyridin-3-yl 2,4-F₂ 1124 2-methoxypyridin-3-yl 2,5-F₂ 11252-methoxypyridin-3-yl 2,6-F₂ 1126 2-methoxypyridin-3-yl 3,4-F₂ 11272-methoxypyridin-3-yl 3,5-F₂ 1128 2-methoxypyridin-3-yl 3,4,5-F₃ 11292-methoxypyridin-3-yl 3-F, 4-Cl 1130 2-methoxypyridin-3-yl 3-F, 4-Br1131 2-methoxypyridin-3-yl 3-CN, 4-F 1132 2-methoxypyridin-3-yl 3-Br,4-F 1133 2-methoxypyridin-3-yl 3-Cl, 4-F 1134 2-methoxypyridin-3-yl3,4-Cl₂ 1135 2-methoxypyridin-4-yl H 1136 2-methoxypyridin-4-yl 2-F 11372-methoxypyridin-4-yl 3-F 1138 2-methoxypyridin-4-yl 4-F 11392-methoxypyridin-4-yl 3-Cl 1140 2-methoxypyridin-4-yl 4-Cl 11412-methoxypyridin-4-yl 3-Br 1142 2-methoxypyridin-4-yl 4-Br 11432-methoxypyridin-4-yl 3-I 1144 2-methoxypyridin-4-yl 3-CN 11452-methoxypyridin-4-yl 4-CN 1146 2-methoxypyridin-4-yl 3-NO₂ 11472-methoxypyridin-4-yl 3-Me 1148 2-methoxypyridin-4-yl 4-Me 11492-methoxypyridin-4-yl 2,3-F₂ 1150 2-methoxypyridin-4-yl 2,4-F₂ 11512-methoxypyridin-4-yl 2,5-F₂ 1152 2-methoxypyridin-4-yl 2,6-F₂ 11532-methoxypyridin-4-yl 3,4-F₂ 1154 2-methoxypyridin-4-yl 3,5-F₂ 11552-methoxypyridin-4-yl 3,4,5-F₃ 1156 2-methoxypyridin-4-yl 3-F, 4-Cl 11572-methoxypyridin-4-yl 3-F, 4-Br 1158 2-methoxypyridin-4-yl 3-CN, 4-F1159 2-methoxypyridin-4-yl 3-Br, 4-F 1160 2-methoxypyridin-4-yl 3-Cl,4-F 1161 2-methoxypyridin-4-yl 3,4-Cl₂ 1162 3-methoxypyridin-4-yl H 11633-methoxypyridin-4-yl 2-F 1164 3-methoxypyridin-4-yl 3-F 11653-methoxypyridin-4-yl 4-F 1166 3-methoxypyridin-4-yl 3-Cl 11673-methoxypyridin-4-yl 4-Cl 1168 3-methoxypyridin-4-yl 3-Br 11693-methoxypyridin-4-yl 4-Br 1170 3-methoxypyridin-4-yl 3-I 11713-methoxypyridin-4-yl 3-CN 1172 3-methoxypyridin-4-yl 4-CN 11733-methoxypyridin-4-yl 3-NO₂ 1174 3-methoxypyridin-4-yl 3-Me 11753-methoxypyridin-4-yl 4-Me 1176 3-methoxypyridin-4-yl 2,3-F₂ 11773-methoxypyridin-4-yl 2,4-F₂ 1178 3-methoxypyridin-4-yl 2,5-F₂ 11793-methoxypyridin-4-yl 2,6-F₂ 1180 3-methoxypyridin-4-yl 3,4-F₂ 11813-methoxypyridin-4-yl 3,5-F₂ 1182 3-methoxypyridin-4-yl 3,4,5-F₃ 11833-methoxypyridin-4-yl 3-F, 4-Cl 1184 3-methoxypyridin-4-yl 3-F, 4-Br1185 3-methoxypyridin-4-yl 3-CN, 4-F 1186 3-methoxypyridin-4-yl 3-Br,4-F 1187 3-methoxypyridin-4-yl 3-Cl, 4-F 1188 3-methoxypyridin-4-yl3,4-Cl₂ 1189 3,5-dichloropyrazin-2-yl H 1190 3,5-dichloropyrazin-2-yl2-F 1191 3,5-dichloropyrazin-2-yl 3-F 1192 3,5-dichloropyrazin-2-yl 4-F1193 3,5-dichloropyrazin-2-yl 3-Cl 1194 3,5-dichloropyrazin-2-yl 4-Cl1195 3,5-dichloropyrazin-2-yl 3-Br 1196 3,5-dichloropyrazin-2-yl 4-Br1197 3,5-dichloropyrazin-2-yl 3-I 1198 3,5-dichloropyrazin-2-yl 3-CN1199 3,5-dichloropyrazin-2-yl 4-CN 1200 3,5-dichloropyrazin-2-yl 3-NO₂1201 3,5-dichloropyrazin-2-yl 3-Me 1202 3,5-dichloropyrazin-2-yl 4-Me1203 3,5-dichloropyrazin-2-yl 2,3-F₂ 1204 3,5-dichloropyrazin-2-yl2,4-F2 1205 3,5-dichloropyrazin-2-yl 2,5-F₂ 12063,5-dichloropyrazin-2-yl 2,6-F₂ 1207 3,5-dichloropyrazin-2-yl 3,4-F₂1208 3,5-dichloropyrazin-2-yl 3,5-F₂ 1209 3,5-dichloropyrazin-2-yl3,4,5-F₃ 1210 3,5-dichloropyrazin-2-yl 3-F, 4-Cl 12113,5-dichloropyrazin-2-yl 3-F, 4-Br 1212 3,5-dichloropyrazin-2-yl 3-CN,4-F 1213 3,5-dichloropyrazin-2-yl 3-Br, 4-F 12143,5-dichloropyrazin-2-yl 3-Cl, 4-F 1215 3,5-dichloropyrazin-2-yl 3,4-Cl₂1216 3,6-dichloropyrazin-2-yl H 1217 3,6-dichloropyrazin-2-yl 2-F 12183,6-dichloropyrazin-2-yl 3-F 1219 3,6-dichloropyrazin-2-yl 4-F 12203,6-dichloropyrazin-2-yl 3-Cl 1221 3,6-dichloropyrazin-2-yl 4-Cl 12223,6-dichloropyrazin-2-yl 3-Br 1223 3,6-dichloropyrazin-2-yl 4-Br 12243,6-dichloropyrazin-2-yl 3-I 1225 3,6-dichloropyrazin-2-yl 3-CN 12263,6-dichloropyrazin-2-yl 4-CN 1227 3,6-dichloropyrazin-2-yl 3-NO₂ 12283,6-dichloropyrazin-2-yl 3-Me 1229 3,6-dichloropyrazin-2-yl 4-Me 12303,6-dichloropyrazin-2-yl 2,3-F₂ 1231 3,6-dichloropyrazin-2-yl 2,4-F21232 3,6-dichloropyrazin-2-yl 2,5-F₂ 1233 3,6-dichloropyrazin-2-yl2,6-F₂ 1234 3,6-dichloropyrazin-2-yl 3,4-F₂ 12353,6-dichloropyrazin-2-yl 3,5-F₂ 1236 3,6-dichloropyrazin-2-yl 3,4,5-F₃1237 3,6-dichloropyrazin-2-yl 3-F, 4-Cl 1238 3,6-dichloropyrazin-2-yl3-F, 4-Br 1239 3,6-dichloropyrazin-2-yl 3-CN, 4-F 12403,6-dichloropyrazin-2-yl 3-Br, 4-F 1241 3,6-dichloropyrazin-2-yl 3-Cl,4-F 1242 3,6-dichloropyrazin-2-yl 3,4-Cl₂ 1243 6-chloropyrazin-2-yl H1244 6-chloropyrazin-2-yl 2-F 1245 6-chloropyrazin-2-yl 3-F 12466-chloropyrazin-2-yl 4-F 1247 6-chloropyrazin-2-yl 3-Cl 12486-chloropyrazin-2-yl 4-Cl 1249 6-chloropyrazin-2-yl 3-Br 12506-chloropyrazin-2-yl 4-Br 1251 6-chloropyrazin-2-yl 3-I 12526-chloropyrazin-2-yl 3-CN 1253 6-chloropyrazin-2-yl 4-CN 12546-chloropyrazin-2-yl 3-NO₂ 1255 6-chloropyrazin-2-yl 3-Me 12566-chloropyrazin-2-yl 4-Me 1257 6-chloropyrazin-2-yl 2,3-F₂ 12586-chloropyrazin-2-yl 2,4-F2 1259 6-chloropyrazin-2-yl 2,5-F₂ 12606-chloropyrazin-2-yl 2,6-F₂ 1261 6-chloropyrazin-2-yl 3,4-F₂ 12626-chloropyrazin-2-yl 3,5-F₂ 1263 6-chloropyrazin-2-yl 3,4,5-F₃ 12646-chloropyrazin-2-yl 3-F, 4-Cl 1265 6-chloropyrazin-2-yl 3-F, 4-Br 12666-chloropyrazin-2-yl 3-CN, 4-F 1267 6-chloropyrazin-2-yl 3-Br, 4-F 12686-chloropyrazin-2-yl 3-Cl, 4-F 1269 6-chloropyrazin-2-yl 3,4-Cl₂ 12705-chloropyrazin-2-yl H 1271 5-chloropyrazin-2-yl 2-F 12725-chloropyrazin-2-yl 3-F 1273 5-chloropyrazin-2-yl 4-F 12745-chloropyrazin-2-yl 3-Cl 1275 5-chloropyrazin-2-yl 4-Cl 12765-chloropyrazin-2-yl 3-Br 1277 5-chloropyrazin-2-yl 4-Br 12785-chloropyrazin-2-yl 3-I 1279 5-chloropyrazin-2-yl 3-CN 12805-chloropyrazin-2-yl 4-CN 1281 5-chloropyrazin-2-yl 3-NO₂ 12825-chloropyrazin-2-yl 3-Me 1283 5-chloropyrazin-2-yl 4-Me 12845-chloropyrazin-2-yl 2,3-F₂ 1285 5-chloropyrazin-2-yl 2,4-F2 12865-chloropyrazin-2-yl 2,5-F₂ 1287 5-chloropyrazin-2-yl 2,6-F₂ 12885-chloropyrazin-2-yl 3,4-F₂ 1289 5-chloropyrazin-2-yl 3,5-F₂ 12905-chloropyrazin-2-yl 3,4,5-F₃ 1291 5-chloropyrazin-2-yl 3-F, 4-Cl 12925-chloropyrazin-2-yl 3-F, 4-Br 1293 5-chloropyrazin-2-yl 3-CN, 4-F 12945-chloropyrazin-2-yl 3-Br, 4-F 1295 5-chloropyrazin-2-yl 3-Cl, 4-F 12965-chloropyrazin-2-yl 3,4-Cl₂ 1297 3-chloropyrazin-2-yl H 12983-chloropyrazin-2-yl 2-F 1299 3-chloropyrazin-2-yl 3-F 13003-chloropyrazin-2-yl 4-F 1301 3-chloropyrazin-2-yl 3-Cl 13023-chloropyrazin-2-yl 4-Cl 1303 3-chloropyrazin-2-yl 3-Br 13043-chloropyrazin-2-yl 4-Br 1305 3-chloropyrazin-2-yl 3-I 13063-chloropyrazin-2-yl 3-CN 1307 3-chloropyrazin-2-yl 4-CN 13083-chloropyrazin-2-yl 3-NO₂ 1309 3-chloropyrazin-2-yl 3-Me 13103-chloropyrazin-2-yl 4-Me 1311 3-chloropyrazin-2-yl 2,3-F₂ 13123-chloropyrazin-2-yl 2,4-F2 1313 3-chloropyrazin-2-yl 2,5-F₂ 13143-chloropyrazin-2-yl 2,6-F₂ 1315 3-chloropyrazin-2-yl 3,4-F₂ 13163-chloropyrazin-2-yl 3,5-F₂ 1317 3-chloropyrazin-2-yl 3,4,5-F₃ 13183-chloropyrazin-2-yl 3-F, 4-Cl 1319 3-chloropyrazin-2-yl 3-F, 4-Br 13203-chloropyrazin-2-yl 3-CN, 4-F 1321 3-chloropyrazin-2-yl 3-Br, 4-F 13223-chloropyrazin-2-yl 3-Cl, 4-F 1323 3-chloropyrazin-2-yl 3,4-Cl₂ 13245-chloro-3-thienyl H 1325 5-chloro-3-thienyl 2-F 1326 5-chloro-3-thienyl3-F 1327 5-chloro-3-thienyl 4-F 1328 5-chloro-3-thienyl 3-Cl 13295-chloro-3-thienyl 4-Cl 1330 5-chloro-3-thienyl 3-Br 13315-chloro-3-thienyl 4-Br 1332 5-chloro-3-thienyl 3-I 13335-chloro-3-thienyl 3-CN 1334 5-chloro-3-thienyl 4-CN 13355-chloro-3-thienyl 3-NO₂ 1336 5-chloro-3-thienyl 3-Me 13375-chloro-3-thienyl 4-Me 1338 5-chloro-3-thienyl 2,3-F₂ 13395-chloro-3-thienyl 2,4-F2 1340 5-chloro-3-thienyl 2,5-F₂ 13415-chloro-3-thienyl 2,6-F₂ 1342 5-chloro-3-thienyl 3,4-F₂ 13435-chloro-3-thienyl 3,5-F₂ 1344 5-chloro-3-thienyl 3,4,5-F₃ 13455-chloro-3-thienyl 3-F, 4-Cl 1346 5-chloro-3-thienyl 3-F, 4-Br 13475-chloro-3-thienyl 3-CN, 4-F 1348 5-chloro-3-thienyl 3-Br, 4-F 13495-chloro-3-thienyl 3-Cl, 4-F 1350 5-chloro-3-thienyl 3,4-Cl₂ 13514-chloro-3-thienyl H 1352 4-chloro-3-thienyl 2-F 1353 4-chloro-3-thienyl3-F 1354 4-chloro-3-thienyl 4-F 1355 4-chloro-3-thienyl 3-Cl 13564-chloro-3-thienyl 4-Cl 1357 4-chloro-3-thienyl 3-Br 13584-chloro-3-thienyl 4-Br 1359 4-chloro-3-thienyl 3-I 13604-chloro-3-thienyl 3-CN 1361 4-chloro-3-thienyl 4-CN 13624-chloro-3-thienyl 3-NO₂ 1363 4-chloro-3-thienyl 3-Me 13644-chloro-3-thienyl 4-Me 1365 4-chloro-3-thienyl 2,3-F₂ 13664-chloro-3-thienyl 2,4-F2 1367 4-chloro-3-thienyl 2,5-F₂ 13684-chloro-3-thienyl 2,6-F₂ 1369 4-chloro-3-thienyl 3,4-F₂ 13704-chloro-3-thienyl 3,5-F₂ 1371 4-chloro-3-thienyl 3,4,5-F₃ 13724-chloro-3-thienyl 3-F, 4-Cl 1373 4-chloro-3-thienyl 3-F, 4-Br 13744-chloro-3-thienyl 3-CN, 4-F 1375 4-chloro-3-thienyl 3-Br, 4-F 13764-chloro-3-thienyl 3-Cl, 4-F 1377 4-chloro-3-thienyl 3,4-Cl₂ 13782-chloro-3-thienyl H 1379 2-chloro-3-thienyl 2-F 1380 2-chloro-3-thienyl3-F 1381 2-chloro-3-thienyl 4-F 1382 2-chloro-3-thienyl 3-Cl 13832-chloro-3-thienyl 4-Cl 1384 2-chloro-3-thienyl 3-Br 13852-chloro-3-thienyl 4-Br 1386 2-chloro-3-thienyl 3-I 13872-chloro-3-thienyl 3-CN 1388 2-chloro-3-thienyl 4-CN 13892-chloro-3-thienyl 3-NO₂ 1390 2-chloro-3-thienyl 3-Me 13912-chloro-3-thienyl 4-Me 1392 2-chloro-3-thienyl 2,3-F₂ 13932-chloro-3-thienyl 2,4-F2 1394 2-chloro-3-thienyl 2,5-F₂ 13952-chloro-3-thienyl 2,6-F₂ 1396 2-chloro-3-thienyl 3,4-F₂ 13972-chloro-3-thienyl 3,5-F₂ 1398 2-chloro-3-thienyl 3,4,5-F₃ 13992-chloro-3-thienyl 3-F, 4-Cl 1400 2-chloro-3-thienyl 3-F, 4-Br 14012-chloro-3-thienyl 3-CN, 4-F 1402 2-chloro-3-thienyl 3-Br, 4-F 14032-chloro-3-thienyl 3-Cl, 4-F 1404 2-chloro-3-thienyl 3,4-Cl₂ 14052,5-dichloro-3-thienyl H 1406 2,5-dichloro-3-thienyl 2-F 14072,5-dichloro-3-thienyl 3-F 1408 2,5-dichloro-3-thienyl 4-F 14092,5-dichloro-3-thienyl 3-Cl 1410 2,5-dichloro-3-thienyl 4-Cl 14112,5-dichloro-3-thienyl 3-Br 1412 2,5-dichloro-3-thienyl 4-Br 14132,5-dichloro-3-thienyl 3-I 1414 2,5-dichloro-3-thienyl 3-CN 14152,5-dichloro-3-thienyl 4-CN 1416 2,5-dichloro-3-thienyl 3-NO₂ 14172,5-dichloro-3-thienyl 3-Me 1418 2,5-dichloro-3-thienyl 4-Me 14192,5-dichloro-3-thienyl 2,3-F₂ 1420 2,5-dichloro-3-thienyl 2,4-F2 14212,5-dichloro-3-thienyl 2,5-F₂ 1422 2,5-dichloro-3-thienyl 2,6-F₂ 14232,5-dichloro-3-thienyl 3,4-F₂ 1424 2,5-dichloro-3-thienyl 3,5-F₂ 14252,5-dichloro-3-thienyl 3,4,5-F₃ 1426 2,5-dichloro-3-thienyl 3-F, 4-Cl1427 2,5-dichloro-3-thienyl 3-F, 4-Br 1428 2,5-dichloro-3-thienyl 3-CN,4-F 1429 2,5-dichloro-3-thienyl 3-Br, 4-F 1430 2,5-dichloro-3-thienyl3-Cl, 4-F 1431 2,5-dichloro-3-thienyl 3,4-Cl₂ 1432 5-chloro-2-thienyl H1433 5-chloro-2-thienyl 2-F 1434 5-chloro-2-thienyl 3-F 14355-chloro-2-thienyl 4-F 1436 5-chloro-2-thienyl 3-Cl 14375-chloro-2-thienyl 4-Cl 1438 5-chloro-2-thienyl 3-Br 14395-chloro-2-thienyl 4-Br 1440 5-chloro-2-thienyl 3-I 14415-chloro-2-thienyl 3-CN 1442 5-chloro-2-thienyl 4-CN 14435-chloro-2-thienyl 3-NO₂ 1444 5-chloro-2-thienyl 3-Me 14455-chloro-2-thienyl 4-Me 1446 5-chloro-2-thienyl 2,3-F₂ 14475-chloro-2-thienyl 2,4-F2 1448 5-chloro-2-thienyl 2,5-F₂ 14495-chloro-2-thienyl 2,6-F₂ 1450 5-chloro-2-thienyl 3,4-F₂ 14515-chloro-2-thienyl 3,5-F₂ 1452 5-chloro-2-thienyl 3,4,5-F₃ 14535-chloro-2-thienyl 3-F, 4-Cl 1454 5-chloro-2-thienyl 3-F, 4-Br 14555-chloro-2-thienyl 3-CN, 4-F 1456 5-chloro-2-thienyl 3-Br, 4-F 14575-chloro-2-thienyl 3-Cl, 4-F 1458 5-chloro-2-thienyl 3,4-Cl₂ 14594-chloro-2-thienyl H 1460 4-chloro-2-thienyl 2-F 1461 4-chloro-2-thienyl3-F 1462 4-chloro-2-thienyl 4-F 1463 4-chloro-2-thienyl 3-Cl 14644-chloro-2-thienyl 4-Cl 1465 4-chloro-2-thienyl 3-Br 14664-chloro-2-thienyl 4-Br 1467 4-chloro-2-thienyl 3-I 14684-chloro-2-thienyl 3-CN 1469 4-chloro-2-thienyl 4-CN 14704-chloro-2-thienyl 3-NO₂ 1471 4-chloro-2-thienyl 3-Me 14724-chloro-2-thienyl 4-Me 1473 4-chloro-2-thienyl 2,3-F₂ 14744-chloro-2-thienyl 2,4-F2 1475 4-chloro-2-thienyl 2,5-F₂ 14764-chloro-2-thienyl 2,6-F₂ 1477 4-chloro-2-thienyl 3,4-F₂ 14784-chloro-2-thienyl 3,5-F₂ 1479 4-chloro-2-thienyl 3,4,5-F₃ 14804-chloro-2-thienyl 3-F, 4-Cl 1481 4-chloro-2-thienyl 3-F, 4-Br 14824-chloro-2-thienyl 3-CN, 4-F 1483 4-chloro-2-thienyl 3-Br, 4-F 14844-chloro-2-thienyl 3-Cl, 4-F 1485 4-chloro-2-thienyl 3,4-Cl₂ 14863-chloro-2-thienyl H 1487 3-chloro-2-thienyl 2-F 1488 3-chloro-2-thienyl3-F 1489 3-chloro-2-thienyl 4-F 1490 3-chloro-2-thienyl 3-Cl 14913-chloro-2-thienyl 4-Cl 1492 3-chloro-2-thienyl 3-Br 14933-chloro-2-thienyl 4-Br 1494 3-chloro-2-thienyl 3-I 14953-chloro-2-thienyl 3-CN 1496 3-chloro-2-thienyl 4-CN 14973-chloro-2-thienyl 3-NO₂ 1498 3-chloro-2-thienyl 3-Me 14993-chloro-2-thienyl 4-Me 1500 3-chloro-2-thienyl 2,3-F₂ 15013-chloro-2-thienyl 2,4-F2 1502 3-chloro-2-thienyl 2,5-F₂ 15033-chloro-2-thienyl 2,6-F₂ 1504 3-chloro-2-thienyl 3,4-F₂ 15053-chloro-2-thienyl 3,5-F₂ 1506 3-chloro-2-thienyl 3,4,5-F₃ 15073-chloro-2-thienyl 3-F, 4-Cl 1508 3-chloro-2-thienyl 3-F, 4-Br 15093-chloro-2-thienyl 3-CN, 4-F 1510 3-chloro-2-thienyl 3-Br, 4-F 15113-chloro-2-thienyl 3-Cl, 4-F 1512 3-chloro-2-thienyl 3,4-Cl₂ 15132-bromo-1,3-thiazol-5-yl H 1514 2-bromo-1,3-thiazol-5-yl 2-F 15152-bromo-1,3-thiazol-5-yl 3-F 1516 2-bromo-1,3-thiazol-5-yl 4-F 15172-bromo-1,3-thiazol-5-yl 3-Cl 1518 2-bromo-1,3-thiazol-5-yl 4-Cl 15192-bromo-1,3-thiazol-5-yl 3-Br 1520 2-bromo-1,3-thiazol-5-yl 4-Br 15212-bromo-1,3-thiazol-5-yl 3-I 1522 2-bromo-1,3-thiazol-5-yl 3-CN 15232-bromo-1,3-thiazol-5-yl 4-CN 1524 2-bromo-1,3-thiazol-5-yl 3-NO₂ 15252-bromo-1,3-thiazol-5-yl 3-Me 1526 2-bromo-1,3-thiazol-5-yl 4-Me 15272-bromo-1,3-thiazol-5-yl 2,3-F₂ 1528 2-bromo-1,3-thiazol-5-yl 2,4-F21529 2-bromo-1,3-thiazol-5-yl 2,5-F₂ 1530 2-bromo-1,3-thiazol-5-yl2,6-F₂ 1531 2-bromo-1,3-thiazol-5-yl 3,4-F₂ 15322-bromo-1,3-thiazol-5-yl 3,5-F₂ 1533 2-bromo-1,3-thiazol-5-yl 3,4,5-F₃1534 2-bromo-1,3-thiazol-5-yl 3-F, 4-Cl 1535 2-bromo-1,3-thiazol-5-yl3-F, 4-Br 1536 2-bromo-1,3-thiazol-5-yl 3-CN, 4-F 15372-bromo-1,3-thiazol-5-yl 3-Br, 4-F 1538 2-bromo-1,3-thiazol-5-yl 3-Cl,4-F 1539 2-bromo-1,3-thiazol-5-yl 3,4-Cl₂ 1540 2-chloro-1,3-thiazol-5-ylH 1541 2-chloro-1,3-thiazol-5-yl 2-F 1542 2-chloro-1,3-thiazol-5-yl 3-F1543 2-chloro-1,3-thiazol-5-yl 4-F 1544 2-chloro-1,3-thiazol-5-yl 3-Cl1545 2-chloro-1,3-thiazol-5-yl 4-Cl 1546 2-chloro-1,3-thiazol-5-yl 3-Br1547 2-chloro-1,3-thiazol-5-yl 4-Br 1548 2-chloro-1,3-thiazol-5-yl 3-I1549 2-chloro-1,3-thiazol-5-yl 3-CN 1550 2-chloro-1,3-thiazol-5-yl 4-CN1551 2-chloro-1,3-thiazol-5-yl 3-NO₂ 1552 2-chloro-1,3-thiazol-5-yl 3-Me1553 2-chloro-1,3-thiazol-5-yl 4-Me 1554 2-chloro-1,3-thiazol-5-yl2,3-F₂ 1555 2-chloro-1,3-thiazol-5-yl 2,4-F2 15562-chloro-1,3-thiazol-5-yl 2,5-F₂ 1557 2-chloro-1,3-thiazol-5-yl 2,6-F₂1558 2-chloro-1,3-thiazol-5-yl 3,4-F₂ 1559 2-chloro-1,3-thiazol-5-yl3,5-F₂ 1560 2-chloro-1,3-thiazol-5-yl 3,4,5-F₃ 15612-chloro-1,3-thiazol-5-yl 3-F, 4-Cl 1562 2-chloro-1,3-thiazol-5-yl 3-F,4-Br 1563 2-chloro-1,3-thiazol-5-yl 3-CN, 4-F 15642-chloro-1,3-thiazol-5-yl 3-Br, 4-F 1565 2-chloro-1,3-thiazol-5-yl 3-Cl,4-F 1566 2-chloro-1,3-thiazol-5-yl 3,4-Cl₂ 1567 5-fluoro-3-thienyl H1568 5-fluoro-3-thienyl 2-F 1569 5-fluoro-3-thienyl 3-F 15705-fluoro-3-thienyl 4-F 1571 5-fluoro-3-thienyl 3-Cl 15725-fluoro-3-thienyl 4-Cl 1573 5-fluoro-3-thienyl 3-Br 15745-fluoro-3-thienyl 4-Br 1575 5-fluoro-3-thienyl 3-I 15765-fluoro-3-thienyl 3-CN 1577 5-fluoro-3-thienyl 4-CN 15785-fluoro-3-thienyl 3-NO₂ 1579 5-fluoro-3-thienyl 3-Me 15805-fluoro-3-thienyl 4-Me 1581 5-fluoro-3-thienyl 2,3-F₂ 15825-fluoro-3-thienyl 2,4-F2 1583 5-fluoro-3-thienyl 2,5-F₂ 15845-fluoro-3-thienyl 2,6-F₂ 1585 5-fluoro-3-thienyl 3,4-F₂ 15865-fluoro-3-thienyl 3,5-F₂ 1587 5-fluoro-3-thienyl 3,4,5-F₃ 15885-fluoro-3-thienyl 3-F, 4-Cl 1589 5-fluoro-3-thienyl 3-F, 4-Br 15905-fluoro-3-thienyl 3-CN, 4-F 1591 5-fluoro-3-thienyl 3-Br, 4-F 15925-fluoro-3-thienyl 3-Cl, 4-F 1593 5-fluoro-3-thienyl 3,4-Cl₂ 15944-fluoro-3-thienyl H 1595 4-fluoro-3-thienyl 2-F 1596 4-fluoro-3-thienyl3-F 1597 4-fluoro-3-thienyl 4-F 1598 4-fluoro-3-thienyl 3-Cl 15994-fluoro-3-thienyl 4-Cl 1600 4-fluoro-3-thienyl 3-Br 16014-fluoro-3-thienyl 4-Br 1602 4-fluoro-3-thienyl 3-I 16034-fluoro-3-thienyl 3-CN 1604 4-fluoro-3-thienyl 4-CN 16054-fluoro-3-thienyl 3-NO₂ 1606 4-fluoro-3-thienyl 3-Me 16074-fluoro-3-thienyl 4-Me 1608 4-fluoro-3-thienyl 2,3-F₂ 16094-fluoro-3-thienyl 2,4-F2 1610 4-fluoro-3-thienyl 2,5-F₂ 16114-fluoro-3-thienyl 2,6-F₂ 1612 4-fluoro-3-thienyl 3,4-F₂ 16134-fluoro-3-thienyl 3,5-F₂ 1614 4-fluoro-3-thienyl 3,4,5-F₃ 16154-fluoro-3-thienyl 3-F, 4-Cl 1616 4-fluoro-3-thienyl 3-F, 4-Br 16174-fluoro-3-thienyl 3-CN, 4-F 1618 4-fluoro-3-thienyl 3-Br, 4-F 16194-fluoro-3-thienyl 3-Cl, 4-F 1620 4-fluoro-3-thienyl 3,4-Cl₂ 16212-fluoro-3-thienyl H 1622 2-fluoro-3-thienyl 2-F 1623 2-fluoro-3-thienyl3-F 1624 2-fluoro-3-thienyl 4-F 1625 2-fluoro-3-thienyl 3-Cl 16262-fluoro-3-thienyl 4-Cl 1627 2-fluoro-3-thienyl 3-Br 16282-fluoro-3-thienyl 4-Br 1629 2-fluoro-3-thienyl 3-I 16302-fluoro-3-thienyl 3-CN 1631 2-fluoro-3-thienyl 4-CN 16322-fluoro-3-thienyl 3-NO₂ 1633 2-fluoro-3-thienyl 3-Me 16342-fluoro-3-thienyl 4-Me 1635 2-fluoro-3-thienyl 2,3-F₂ 16362-fluoro-3-thienyl 2,4-F2 1637 2-fluoro-3-thienyl 2,5-F₂ 16382-fluoro-3-thienyl 2,6-F₂ 1639 2-fluoro-3-thienyl 3,4-F₂ 16402-fluoro-3-thienyl 3,5-F₂ 1641 2-fluoro-3-thienyl 3,4,5-F₃ 16422-fluoro-3-thienyl 3-F, 4-Cl 1643 2-fluoro-3-thienyl 3-F, 4-Br 16442-fluoro-3-thienyl 3-CN, 4-F 1645 2-fluoro-3-thienyl 3-Br, 4-F 16462-fluoro-3-thienyl 3-Cl, 4-F 1647 2-fluoro-3-thienyl 3,4-Cl₂ 16482,5-difluoro-3-thienyl H 1649 2,5-difluoro-3-thienyl 2-F 16502,5-difluoro-3-thienyl 3-F 1651 2,5-difluoro-3-thienyl 4-F 16522,5-difluoro-3-thienyl 3-Cl 1653 2,5-difluoro-3-thienyl 4-Cl 16542,5-difluoro-3-thienyl 3-Br 1655 2,5-difluoro-3-thienyl 4-Br 16562,5-difluoro-3-thienyl 3-I 1657 2,5-difluoro-3-thienyl 3-CN 16582,5-difluoro-3-thienyl 4-CN 1659 2,5-difluoro-3-thienyl 3-NO₂ 16602,5-difluoro-3-thienyl 3-Me 1661 2,5-difluoro-3-thienyl 4-Me 16622,5-difluoro-3-thienyl 2,3-F₂ 1663 2,5-difluoro-3-thienyl 2,4-F2 16642,5-difluoro-3-thienyl 2,5-F₂ 1665 2,5-difluoro-3-thienyl 2,6-F₂ 16662,5-difluoro-3-thienyl 3,4-F₂ 1667 2,5-difluoro-3-thienyl 3,5-F₂ 16682,5-difluoro-3-thienyl 3,4,5-F₃ 1669 2,5-difluoro-3-thienyl 3-F, 4-Cl1670 2,5-difluoro-3-thienyl 3-F, 4-Br 1671 2,5-difluoro-3-thienyl 3-CN,4-F 1672 2,5-difluoro-3-thienyl 3-Br, 4-F 1673 2,5-difluoro-3-thienyl3-Cl, 4-F 1674 2,5-difluoro-3-thienyl 3,4-Cl₂ 1675 5-fluoro-2-thienyl H1676 5-fluoro-2-thienyl 2-F 1677 5-fluoro-2-thienyl 3-F 16785-fluoro-2-thienyl 4-F 1679 5-fluoro-2-thienyl 3-Cl 16805-fluoro-2-thienyl 4-Cl 1681 5-fluoro-2-thienyl 3-Br 16825-fluoro-2-thienyl 4-Br 1683 5-fluoro-2-thienyl 3-I 16845-fluoro-2-thienyl 3-CN 1685 5-fluoro-2-thienyl 4-CN 16865-fluoro-2-thienyl 3-NO₂ 1687 5-fluoro-2-thienyl 3-Me 16885-fluoro-2-thienyl 4-Me 1689 5-fluoro-2-thienyl 2,3-F₂ 16905-fluoro-2-thienyl 2,4-F2 1691 5-fluoro-2-thienyl 2,5-F₂ 16925-fluoro-2-thienyl 2,6-F₂ 1693 5-fluoro-2-thienyl 3,4-F₂ 16945-fluoro-2-thienyl 3,5-F₂ 1695 5-fluoro-2-thienyl 3,4,5-F₃ 16965-fluoro-2-thienyl 3-F, 4-Cl 1697 5-fluoro-2-thienyl 3-F, 4-Br 16985-fluoro-2-thienyl 3-CN, 4-F 1699 5-fluoro-2-thienyl 3-Br, 4-F 17005-fluoro-2-thienyl 3-Cl, 4-F 1701 5-fluoro-2-thienyl 3,4-Cl₂ 17024-fluoro-2-thienyl H 1703 4-fluoro-2-thienyl 2-F 1704 4-fluoro-2-thienyl3-F 1705 4-fluoro-2-thienyl 4-F 1706 4-fluoro-2-thienyl 3-Cl 17074-fluoro-2-thienyl 4-Cl 1708 4-fluoro-2-thienyl 3-Br 17094-fluoro-2-thienyl 4-Br 1710 4-fluoro-2-thienyl 3-I 17114-fluoro-2-thienyl 3-CN 1712 4-fluoro-2-thienyl 4-CN 17134-fluoro-2-thienyl 3-NO₂ 1714 4-fluoro-2-thienyl 3-Me 17154-fluoro-2-thienyl 4-Me 1716 4-fluoro-2-thienyl 2,3-F₂ 17174-fluoro-2-thienyl 2,4-F2 1718 4-fluoro-2-thienyl 2,5-F₂ 17194-fluoro-2-thienyl 2,6-F₂ 1720 4-fluoro-2-thienyl 3,4-F₂ 17214-fluoro-2-thienyl 3,5-F₂ 1722 4-fluoro-2-thienyl 3,4,5-F₃ 17234-fluoro-2-thienyl 3-F, 4-Cl 1724 4-fluoro-2-thienyl 3-F, 4-Br 17254-fluoro-2-thienyl 3-CN, 4-F 1726 4-fluoro-2-thienyl 3-Br, 4-F 17274-fluoro-2-thienyl 3-Cl, 4-F 1728 4-fluoro-2-thienyl 3,4-Cl₂ 17293-fluoro-2-thienyl H 1730 3-fluoro-2-thienyl 2-F 1731 3-fluoro-2-thienyl3-F 1732 3-fluoro-2-thienyl 4-F 1733 3-fluoro-2-thienyl 3-Cl 17343-fluoro-2-thienyl 4-Cl 1735 3-fluoro-2-thienyl 3-Br 17363-fluoro-2-thienyl 4-Br 1737 3-fluoro-2-thienyl 3-I 17383-fluoro-2-thienyl 3-CN 1739 3-fluoro-2-thienyl 4-CN 17403-fluoro-2-thienyl 3-NO₂ 1741 3-fluoro-2-thienyl 3-Me 17423-fluoro-2-thienyl 4-Me 1743 3-fluoro-2-thienyl 2,3-F₂ 17443-fluoro-2-thienyl 2,4-F2 1745 3-fluoro-2-thienyl 2,5-F₂ 17463-fluoro-2-thienyl 2,6-F₂ 1747 3-fluoro-2-thienyl 3,4-F₂ 17483-fluoro-2-thienyl 3,5-F₂ 1749 3-fluoro-2-thienyl 3,4,5-F₃ 17503-fluoro-2-thienyl 3-F, 4-Cl 1751 3-fluoro-2-thienyl 3-F, 4-Br 17523-fluoro-2-thienyl 3-CN, 4-F 1753 3-fluoro-2-thienyl 3-Br, 4-F 17543-fluoro-2-thienyl 3-Cl, 4-F 1755 3-fluoro-2-thienyl 3,4-Cl₂ 17561,3-thiazol-5-yl H 1757 1,3-thiazol-5-yl 2-F 1758 1,3-thiazol-5-yl 3-F1759 1,3-thiazol-5-yl 4-F 1760 1,3-thiazol-5-yl 3-Cl 17611,3-thiazol-5-yl 4-Cl 1762 1,3-thiazol-5-yl 3-Br 1763 1,3-thiazol-5-yl4-Br 1764 1,3-thiazol-5-yl 3-I 1765 1,3-thiazol-5-yl 3-CN 17661,3-thiazol-5-yl 4-CN 1767 1,3-thiazol-5-yl 3-NO₂ 1768 1,3-thiazol-5-yl3-Me 1769 1,3-thiazol-5-yl 4-Me 1770 1,3-thiazol-5-yl 2,3-F₂ 17711,3-thiazol-5-yl 2,4-F2 1772 1,3-thiazol-5-yl 2,5-F₂ 17731,3-thiazol-5-yl 2,6-F₂ 1774 1,3-thiazol-5-yl 3,4-F₂ 17751,3-thiazol-5-yl 3,5-F₂ 1776 1,3-thiazol-5-yl 3,4,5-F₃ 17771,3-thiazol-5-yl 3-F, 4-Cl 1778 1,3-thiazol-5-yl 3-F, 4-Br 17791,3-thiazol-5-yl 3-CN, 4-F 1780 1,3-thiazol-5-yl 3-Br, 4-F 17811,3-thiazol-5-yl 3-Cl, 4-F 1782 1,3-thiazol-5-yl 3,4-Cl₂ 17831,3-oxazol-5-yl H 1784 1,3-oxazol-5-yl 2-F 1785 1,3-oxazol-5-yl 3-F 17861,3-oxazol-5-yl 4-F 1787 1,3-oxazol-5-yl 3-Cl 1788 1,3-oxazol-5-yl 4-Cl1789 1,3-oxazol-5-yl 3-Br 1790 1,3-oxazol-5-yl 4-Br 1791 1,3-oxazol-5-yl3-I 1792 1,3-oxazol-5-yl 3-CN 1793 1,3-oxazol-5-yl 4-CN 17941,3-oxazol-5-yl 3-NO₂ 1795 1,3-oxazol-5-yl 3-Me 1796 1,3-oxazol-5-yl4-Me 1797 1,3-oxazol-5-yl 2,3-F₂ 1798 1,3-oxazol-5-yl 2,4-F2 17991,3-oxazol-5-yl 2,5-F₂ 1800 1,3-oxazol-5-yl 2,6-F₂ 1801 1,3-oxazol-5-yl3,4-F₂ 1802 1,3-oxazol-5-yl 3,5-F₂ 1803 1,3-oxazol-5-yl 3,4,5-F₃ 18041,3-oxazol-5-yl 3-F, 4-Cl 1805 1,3-oxazol-5-yl 3-F, 4-Br 18061,3-oxazol-5-yl 3-CN, 4-F 1807 1,3-oxazol-5-yl 3-Br, 4-F 18081,3-oxazol-5-yl 3-Cl, 4-F 1809 1,3-oxazol-5-yl 3,4-Cl₂

Likewise preferred compounds of the formula (I) or (Ia) according to theinvention are described in the Example section below.

For preferred compounds of the formula (I) or (Ia) according to theinvention, m is greater than or equal to 1, preferably greater than orequal to 2, and the following applies:

one, more than one or all radicals R² are selected from the groupconsisting of F, Cl, Br, I, methyl and CN,

and

one, more than one or all radicals R³ are selected from the groupconsisting of F, Cl, Br, methyl, methoxy, nitro and CN.

For preferred compounds of the formula (I) or (Ia) according to theinvention, the following applies:

n is greater than or equal to 1, preferably greater than or equal to 2,

m is greater than or equal to 1, preferably greater than or equal to 2,

one, more than one or all radicals R² are selected from the groupconsisting of F, Cl, Br, I, methyl and CN,

and

one, more than one or all radicals R³ are selected from the groupconsisting of F, Cl, Br, methyl, methoxy and CN.

Particular preference according to the invention is given to compoundsof the formula (I) or (Ia) or salts thereof where the following applies:

n=1, 2 or 3, and at least one R² is selected, preferably all R² areselected, from the group consisting of fluorine, chlorine and bromine,

and/or

m=1, 2 or 3, and at least one R³ is selected, preferably all R³ areselected, from the group consisting of fluorine and chlorine.

Likewise preferred according to the invention are compounds of theformula (I) and/or salts thereof in which (R³)_(m) is 3-chloro,4-chloro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro,3,4-dichloro, 3,5-dichloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro,2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro,2,3,6-trifluoro, 2,4,6-trifluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),(3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F) or (2,6-F₂-4-Cl).

Likewise preferred according to the invention are compounds of theformula (Ia) and/or salts thereof in which (R³)_(m) is 3-chloro,4-chloro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro,3,4-dichloro, 3,5-dichloro, 2-fluoro, 3-fluoro, 4-fluoro, 2,3-difluoro,2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro,2,3,6-trifluoro, 2,4,6-trifluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),(3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F) or (2,6-F₂-4-Cl).

Among the compounds according to the invention with the meanings givenabove, preference is given to those in which the structural element Q,R¹, (R²)_(n) and (R³)_(m) defined in each case as preferred, in eachcase as particularly preferred or in each case as especially preferredare realized in combination with one another.

The compounds of the formula (I) according to the invention can have(2,3)-erythro configuration, i.e. correspond to the compounds of thefollowing formulae (I eryrthro-1) and (I eryrthro-2):

Furthermore, it has been found that the compounds of the formula (I)according to the invention and/or their salts or (Ia) and/or their saltswhich are (2,3)-threo-configured have better herbicidal properties thanthe corresponding (2,3)-erythro-configured compounds. Accordingly,(2,3)-threo-configured compounds of the formulae (I) and (Ia) and theirsalts are preferred. The same applies accordingly to compositionsaccording to the invention.

Accordingly, preference according to the invention is given to mixturesand compositions in which the molar ratio of a (2,3)-threo-configuredcompound of the formula (I) to the corresponding(2,3)-erythro-configured compound of the formula (I) is greater than 1,more preferably greater than 2, particularly preferably greater than 3and especially preferably greater than 4.

Likewise, preference according to the invention is given to mixtures andcompositions in which the weight ratio of the total amount of(2,3)-threo-configured compounds of the formulae (I) and (Ia) to thetotal amount of (2,3)-erythro-configured compounds of the formulae (I)and (Ia) is greater than 1, more preferably greater than 2, particularlypreferably greater than 3 and especially preferably greater than 4.

Surprisingly, it has furthermore been found that optically activethreo-configured compounds of the formula (I) and their salts haveparticularly good herbicidal activities and at the same timeadvantageous selectivities with respect to some useful plants.

Accordingly, in the context of the present invention preference is givento compounds of the formula (I) and their salts having a(2,3)-threo-configuration, i.e. compounds of the following formulae (Ithreo-1) and (I threo-2)

in which

R¹, R², R³, n and m each have the meaning mentioned above, preferablyone of the meanings given in each case as being preferred orparticularly preferred.

In the context of the present invention preference is given to compoundsof the formula (Ia) and their salts having a (2,3)-threo-configuration,i.e. compounds of the following formulae (Ia threo-1) and/or (Iathreo-2)

in which

R², R³, n and m each have the meaning mentioned above, preferably one ofthe meanings given in each case as being preferred or particularlypreferred or especially preferred.

The stereochemical configuration at the carbon atom in position 2 of thepentanonitrile derivative of the formulae (I) and (Ia) preferably has astereochemical purity of from 60 to 100% (S), with preference from 70 to100% (S), more preferably from 80 to 100% (S), especially preferablyfrom 90 to 100% (S), and the stereochemical configuration at the carbonatom in position 3 of the pentanonitrile derivative preferably has astereochemical purity of from 60 to 100% (5), with preference from 70 to100% (S), more preferably from 80 to 100% (S), especially preferablyfrom 90 to 100% (S), in each case based on the total amount of thethreo-enantiomers in question.

The stereochemical configuration at the carbon atom in position 2 of thepentanonitrile derivative of the formulae (I) and (Ia) preferably has astereochemical purity of from 60 to 100% (R), with preference from 70 to100% (R), more preferably from 80 to 100% (R), especially preferablyfrom 90 to 100% (R), and the stereochemical configuration at the carbonatom in position 3 of the pentanonitrile derivative preferably has astereochemical purity of from 60 to 100% (R), with preference from 70 to100% (R), more preferably from 80 to 100% (R), especially preferablyfrom 90 to 100% (R), in each case based on the total amount of thethreo-enantiomers in question.

By virtue of their even better property profile, in particular theireven better herbicidal activity, special preference is given to the(2R,3R)-configured pentanonitrile derivatives of the formulae (I) and(Ia), preferably in the stereochemical purities stated above. As aconsequence, compounds of the formulae (I threo-1) and (Ia threo-1) areparticularly preferred in the context of the present invention. Theabsolute configuration of these (2R,3R)-configured pentanonitrilederivatives was assigned by X-ray structural analysis.

That stated above applies accordingly to mixtures according to theinvention and compositions according to the invention.

The compounds of the formula (I) according to the invention can beprepared by various processes.

In the processes described below, in some cases solvents are employed.In this context, “inert solvents” refers in each case to solvents whichare inert under the particular reaction conditions, but which do nothave to be inert under any reaction conditions. In the processes below,the reactions described can alternatively also be carried out in amicrowave reactor.

The compounds according to the invention can be prepared by methodsknown per se. Here, the starting material may, for example, be compoundsof the formula (E). Compounds of the formula (E) are known from theprior art, for example from WO 2014/095879 A1. The scheme below shows,in an exemplary manner, how the compounds according to the invention canbe prepared.

Here, R¹, R², R³, n and m each have the (preferred or particularlypreferred) meaning mentioned above, and R represents hydrogen or anorganic radical, preferably a radical selected from the group of theradicals defined above for R¹.

With respect to “Step 1” of the above scheme:

Methods for the selective reduction of compounds of the formula (E) togive corresponding compounds of the formula (Ia) are known to the personskilled in the art from the prior art and described, for example, inEuropean Journal of Organic Chemistry 2009, (11), 1806-1811 or in WO2012/076513 A1. Preferably, the selective reduction in this case iscarried out using borohydrides, with preference using borohydrides ofalkali metal borohydrides, in particular of lithium borohydride, sodiumborohydride or potassium borohydride, and in turn preferably in thepresence of a lithium halide, preferably in the presence of lithiumchloride. Here, this reduction can be carried out in a protic organicsolvent such as, for example, ethanol (see, for example, WO2011/014383), or an aprotic organic solvent such as, for example,tetrahydrofuran (THF), here preferably by heating under reflux.

With respect to “Step 2” of the above scheme:

The present optional further reaction (nucleophilic substitution) of theprimary alcohol (Ia) obtained in “Step 1” with R¹—X¹ (where X¹represents a leaving group) to give compounds of the formula (I) isknown in principle to the person skilled in the art and described, forexample, in Journal of Organic Chemistry 2011, 76(3), 811-819. Here, thenucleophilic substitution is preferably carried out in the presence of4-(dimethylamino)pyridine. The reaction can also be carried out, forexample, in an aprotic organic solvent such as tetrahydrofuran (THF) ordichloromethane, if appropriate at elevated temperature, for example byheating under reflux.

Accordingly, the present invention also relates to a process forpreparing a compound of the formula (I) according to the inventionand/or a salt thereof, characterized in that a compound of the formula(E)

is converted by reduction into a compound of the formula (Ia)

and the compound (Ia) is optionally reacted further to give a compoundof the formula (I), provided R¹ does not represent hydrogen,

where

R represents hydrogen or an organic radical, preferably a radicalselected from the group of the radicals defined above for R¹, withpreference selected from one of the radicals characterized as beingpreferred, and

R², R³, m and n each have the meaning defined above, and are preferablyin each case selected from one of the groups of radicals characterizedas being preferred.

The starting materials (E) used for preparing the compounds of theformula (Ia) or (I) are known from the literature cited or can beprepared analogously to the literature cited.

To prepare the compounds (Ia) or (I) according to the invention, it isalso possible to use the corresponding diastereomer mixtures in the formof their racemic mixtures.

If stereochemically enriched compounds of the formula (E) mentionedabove are used in the process according to the invention, it is possibleto obtain the corresponding stereochemically enriched compounds of theformula (Ia) or (I).

Solvents suitable for this purpose are, for example, organic solventssuch as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or        petroleum ether;    -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,    -   halogenated hydrocarbons such as methylene chloride, chloroform        or chlorobenzene,    -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl        methyl ether, dioxane, anisole and tetrahydrofuran (THF),    -   nitriles such as acetonitrile or propionitrile,    -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and        tert-butyl methyl ketone,    -   dimethyl sulfoxide, dimethylformamide, dimethylacetamide,        sulfolane, and also    -   mixtures of the stated organic solvents.

In individual cases, it is also appropriate to use inorganic solventssuch as water or mixtures of organic solvents with water.

Suitable conditions and catalysts for the preparation of compounds ofthe formula (I) in which R¹ does not represent H from compounds of theformula (Ia), for example by esterification, are known to the personskilled in the art.

The conversion of compounds of the formula (Ia) into compounds of theformula (I) in which R¹ does not represent H can be carried out in thepresence of a base, for example a base from the group of the inorganicbases such as the alkali metal and alkaline earth metal hydroxides, forexample lithium hydroxide, sodium hydroxide, potassium hydroxide orcalcium hydroxide, the alkali metal and alkaline earth metal oxides, forexample lithium oxide, sodium oxide, calcium oxide or magnesium oxide,the alkali metal and alkaline earth metal hydrides, for example lithiumhydride, sodium hydride, potassium hydride or calcium hydride, thealkali metal amides, for example lithium amide, sodium amide orpotassium amide, the alkali metal and alkaline earth metal carbonates,for example lithium carbonate, potassium carbonate or calcium carbonate,the alkali metal bicarbonates, for example sodium bicarbonate, or theorganometallic compounds such as, preferably, the alkali metal alkyls,for example methyllithium, butyllithium or phenyllithium, thealkylmagnesium halides, for example methylmagnesium chloride, or thealkali metal and alkaline earth metal alkoxides, for example sodiummethoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxideor dimethoxymagnesium.

The bases used can also be organic bases, for example from the group ofthe tertiary aliphatic amines, for example trimethylamine,triethylamine, tributylamine, diisopropylethylamine orN-methylpiperidine, or the aromatic tertiary amines, for examplepyridine or substituted pyridines such as collidine, lutidine or4-dimethylaminopyridine, or the bicyclic amines such as7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene or1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

Preferred bases are, for example, lithium hydroxide, potassiumcarbonate, potassium tert-butoxide, lithium bis(trimethylsilyl)amide,pyridines, substituted pyridines,7-methyl-1,5,7-triazabicyclo[4.4.0]-dec-5-ene or DBU.

The amount of base may generally vary within wide limits. For example,it may be expedient to employ the base in catalytic amounts, insubstoichiometric amounts, in equimolar amounts or in excess. Apreferably liquid organic base may optionally also be used as solvent.

Suitable catalysts for the conversion of compounds of the formula (Ia)into compounds of the formula (I) in which R¹ is not H may also beacidic catalysts, for example from the group of the inorganic acids, forexample Broensted acids, such as hydrofluoric acid, hydrochloric acid,hydrobromic acid, sulfuric acid or perchloric acid, or Lewis acids, suchas boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV)chloride, titanium(IV) chloride, scandium(III) triflate or zinc(II)chloride, and also organic acids, for example formic acid, acetic acid,propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid,camphorsulfonic acid, citric acid or trifluoroacetic acid.

The reaction mixtures obtained are worked up in a customary manner, forexample by mixing with water, separating the phases and optionallychromatographic purification of the crude products. Some of thecompounds are obtained in the form of colorless or slightly brownishviscous oils which are purified or freed from volatile components underreduced pressure and at moderately elevated temperature.

If the compounds are obtained as solids, the purification can also becarried out by recrystallization or digestion. If individual compounds(I) cannot be obtained in a satisfactory manner by the routes describedabove, they can be prepared by derivatization of other compounds (I) or(Ia).

Suitable isolation methods, purification methods and methods forseparating stereoisomers of compounds of the formula (I) or (Ia) aremethods generally known to the person skilled in the art from analogouscases, for example by physical processes such as crystallization,chromatographic methods, in particular column chromatography and HPLC(high pressure liquid chromatography), distillation, optionally underreduced pressure, extraction and other methods, any mixtures that remaincan generally be separated by chromatographic separation, for example onchiral solid phases. Suitable for preparative amounts or on anindustrial scale are processes such as crystallization, for example ofdiastereomeric salts which can be obtained from the diastereomermixtures using optically active acids and, if appropriate, provided thatacidic groups are present, using optically active bases.

Optically active acids which are suitable for optical resolution bycrystallization of diastereomeric salts are, for example,camphorsulfonic acid, camphoric acid, bromocamphorsulfonic acid, quinicacid, tartaric acid, dibenzoyltartaric acid and other analogous acids;suitable optically active bases are, for example, quinine, cinchonine,quinidine, brucine, 1-(S)- or 1-(R)-phenylethylamine and other analogousbases.

The crystallizations are then in most cases carried out in aqueous,alcoholic or aqueous-organic solvents, where the diastereomer which isless soluble precipitates first, if appropriate after seeding. Oneenantiomer of the compound of the formula (I) is then liberated from theprecipitated salt, or the other is liberated from the crystallizate, byacidification or using a base.

As an alternative to the optical resolution methods mentioned,enantioselective processes starting with stereochemically pure startingmaterials are in principle also suitable for preparing the (threo)enantiomers.

The following acids are generally suitable for preparing the acidaddition salts of the compounds of the formula (I): hydrohalic acids,such as hydrochloric acid or hydrobromic acid, furthermore phosphoricacid, nitric acid, sulfuric acid, mono- or bifunctional carboxylic acidsand hydroxycarboxylic acids, such as acetic acid, maleic acid, succinicacid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbicacid, or lactic acid, and also sulfonic acids, such as p-toluenesulfonicacid and 1,5-naphthalenedisulfonic acid. The acid addition compounds ofthe formula (I) can be obtained in a manner known per se by thecustomary methods for forming salts, for example by dissolving acompound of the formula (I) in a suitable organic solvent, such as, forexample, methanol, acetone, methylene chloride or benzene, and addingthe acid at temperatures of from 0 to 100° C., and they can be isolatedin a known manner, for example by filtration, and, if appropriate,purified by washing with an inert organic solvent.

Base addition salts of the compounds of the formula (I) can be prepared,for example, in polar solvents such as, for example, water, methanol oracetone, at temperatures of from 0 to 100° C. Examples of bases whichare suitable for the preparation of such salts are, for example, alkalimetal carbonates, such as potassium carbonate, alkali metal hydroxidesand alkaline earth metal hydroxides, for example NaOH or KOH, alkalimetal hydrides and alkaline earth metal hydrides, for example NaH,alkali metal alkoxides and alkaline earth metal alkoxides, for examplesodium methoxide or potassium tert-butoxide, or ammonia, ethanolamine orquaternary ammonium hydroxide.

A collection of compounds of the formula (I) can additionally beprepared in a parallel or combinatorial manner, it being possible forthis to take place in a manual, partly automated or completely automatedmanner. In this connection, it is possible to automate the reactionprocedure, the work-up or the purification of the products and/orintermediates.

For the parallelized reaction procedure and work-up it is possible touse a range of commercially available instruments, of the kind offeredby, for example, the companies Stem Corporation, Woodrolfe Road,Tollesbury, Essex, CM9 8SE, England, or H+P Labortechnik GmbH,Bruckmannring 28, 85764 Oberschleißheim, Germany. For the parallelizedpurification of compounds (I) or of intermediates produced during thepreparation, there are available, inter alia, chromatographyapparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln,Nebr. 68504, USA. The apparatuses listed allow a modular procedure inwhich the individual process steps are automated, but between theprocess steps manual operations have to be carried out. This can becircumvented by using partly or completely integrated automation systemsin which the respective automation modules are operated, for example, byrobots. Automation systems of this type can be acquired, for example,from Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

Besides the methods described, the preparation of compounds of theformula (I) can take place completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bonded to a synthesis resin.Solid-phase-supported synthesis methods are described extensively in thespecialist literature, for example: Barry A. Bunin in “The CombinatorialIndex”, Verlag Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a number ofprotocols, which are known from the literature and which for their partmay be performed manually or in an automated manner. For example, theso-called “tea bag method” (U.S. Pat. No. 4,631,211) in which productsfrom IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, USA,are employed, may be semiautomated. The automation ofsolid-phase-supported parallel syntheses is performed successfully, forexample, by apparatuses from Argonaut Technologies, Inc., 887 IndustrialRoad, San Carlos, Calif. 94070, USA or MultiSynTech GmbH, Wullener Feld4, 58454 Witten, Germany.

The preparation according to the processes described herein producescompounds of the formula (I) in the form of substance collections orlibraries. Accordingly, the present invention also provides libraries ofcompounds of the formula (I) which comprise at least two compounds ofthe formula (I), and precursors thereof.

The present invention furthermore provides a method for controllingharmful plants and/or for regulating the growth of plants, characterizedin that an effective amount

-   -   of one or more compounds of the formula (I) and/or salts        thereof, as defined above,    -   of one or more compounds of the formula (Ia) and/or salts        thereof, as defined above,

or

-   -   of a composition, as defined above,

is applied to the (harmful) plants, seeds of (harmful) plants, the soilin which or on which the (harmful) plants grow or the area undercultivation.

The present invention also provides a method for controlling unwantedplants, preferably in crops of useful plants, characterized in that aneffective amount

-   -   of one or more compounds of the formula (I) and/or salts        thereof, as defined above,    -   of one or more compounds of the formula (Ia) and/or salts        thereof, as defined above, or    -   of a composition according to the invention, as defined above,

is applied to unwanted plants (for example harmful plants such as mono-or dicotyledonous weeds or unwanted crop plants), the seed of theunwanted plants (i.e. plant seeds, for example grains, seeds orvegetative propagation organs such as tubers or shoot parts with buds),the soil in which or on which the unwanted plants grow (for example thesoil of crop land or non-crop land) or the area under cultivation (i.e.the area on which the unwanted plants will grow).

The present invention furthermore also provides methods for regulatingthe growth of plants, preferably of useful plants, characterized in thatan effective amount

-   -   of one or more compounds of the formula (I) and/or salts        thereof, as defined above,    -   of one or more compounds of the formula (Ia) and/or salts        thereof, as defined above, or    -   of a composition according to the invention, as defined above,

is applied to the plant, the seed of the plant (i.e. plant seed, forexample grains, seeds or vegetative propagation organs such as tubers orshoot parts with buds), the soil in which or on which the plants grow(for example the soil of crop land or non-crop land) or the area undercultivation (i.e. the area on which the plants will grow).

In this context, the compounds according to the invention or thecompositions according to the invention can be applied for example bypre-sowing (if appropriate also by incorporation into the soil),pre-emergence and/or post-emergence processes. Specific examples of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the compounds of the invention are asfollows, though there is no intention to restrict the enumeration toparticular species.

In a method according to the invention for controlling harmful plants orfor regulating the growth of plants, one or more compounds of theformula (I), (Ia) and/or salts thereof are preferably employed forcontrolling harmful plants or for regulating growth in crops of usefulplants or ornamental plants, where in a preferred embodiment the usefulplants or ornamental plants are transgenic plants.

The compounds of the formula (I) or (Ia) according to the inventionand/or their salts are suitable for controlling the following genera ofmonocotyledonous and dicotyledonous harmful plants:

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria and Sorghum.

Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens,Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus,Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga,Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia,Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis,Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala,Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus,Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola and Xanthium.

When the compounds according to the invention are applied to the soilsurface before germination of the harmful plants (weed grasses and/orbroad-leaved weeds) (pre-emergence method), either the seedlings of theweed grasses or broad-leaved weeds are prevented completely fromemerging or they grow until they have reached the cotyledon stage, butthen stop growing and eventually, after three to four weeks haveelapsed, die completely.

If the active ingredients are applied post-emergence to the green partsof the plants, growth stops after the treatment, and the harmful plantsremain at the growth stage at the time of application, or they diecompletely after a certain time, such that competition by the weeds,which is harmful to the crop plants, is thus eliminated very early andin a lasting manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia,or monocotyledonous crops of the genera Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, triticale,triticum, Zea, are damaged only to an insignificant extent, or not atall, depending on the structure of the respective compound according tothe invention and its application rate. For these reasons, the presentcompounds are very suitable for selective control of unwanted plantgrowth in plant crops such as agriculturally useful plants or ornamentalplants.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They intervenein the plants' own metabolism with regulatory effect, and can thus beused for the controlled influencing of plant constituents and tofacilitate harvesting, for example by triggering desiccation and stuntedgrowth. Furthermore, they are also suitable for the general control andinhibition of unwanted vegetative growth without killing the plants inthe process. Inhibition of vegetative growth plays a major role for manymono- and dicotyledonous crops since, for example, this can reduce orcompletely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties,the active ingredients can also be used to control harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or pathogens of plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other specificcharacteristics relate, for example, to the harvested material withregard to quantity, quality, storability, composition and specificconstituents. For instance, there are known transgenic plants with anelevated starch content or altered starch quality, or those with adifferent fatty acid composition in the harvested material.

It is preferred with a view to transgenic crops to use the compoundsaccording to the invention and/or their salts in economically importanttransgenic crops of useful plants and ornamentals, for example ofcereals such as wheat, barley, rye, oats, millet, rice and maize or elsecrops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peasand other vegetables.

It is preferred to employ the compounds according to the invention asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

By virtue of their herbicidal and plant growth regulatory properties,the active ingredients can also be used to control harmful plants incrops of genetically modified plants which are known or are yet to bedeveloped. In general, the transgenic plants are characterized byparticular advantageous properties, for example by resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or pathogens of plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other specificcharacteristics relate, for example, to the harvested material withregard to quantity, quality, storability, composition and specificconstituents. For instance, there are known transgenic plants with anelevated starch content or altered starch quality, or those with adifferent fatty acid composition in the harvested material. Furtherspecial properties may be tolerance or resistance to abiotic stressors,for example heat, cold, drought, salinity and ultraviolet radiation.

Preference is given to the use of the compounds of the formula (I)according to the invention or salts thereof in economically importanttransgenic crops of useful plants and ornamental plants, for example ofcereals such as wheat, barley, rye, oats, triticale, millet, rice,cassava and corn, or else crops of sugar beet, cotton, soybean, oilseedrape, potatoes, tomatoes, peas and other vegetables.

The compounds of the formula (I) can preferably be used as herbicides incrops of useful plants which are resistant, or have been made resistantby recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to existing plants consist, for example, intraditional cultivation methods and the generation of mutants.Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods.

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown to the person skilled in the art. For such recombinantmanipulations, nucleic acid molecules which allow mutagenesis orsequence alteration by recombination of DNA sequences can be introducedinto plasmids. With the aid of standard methods, it is possible, forexample, to undertake base exchanges, remove parts of sequences or addnatural or synthetic sequences. To connect the DNA fragments to eachother, adapters or linkers may be added to the fragments.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect, or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product.

To this end, it is firstly possible to use DNA molecules which encompassthe entire coding sequence of a gene product inclusive of any flankingsequences which may be present, and also DNA molecules which onlyencompass portions of the coding sequence, in which case it is necessaryfor these portions to be long enough to have an antisense effect in thecells. It is also possible to use DNA sequences which have a high degreeof homology to the coding sequences of a gene product, but are notcompletely identical to them.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also beexpressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants may beplants of any desired plant species, i.e. not only monocotyledonous butalso dicotyledonous plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or expression of heterologous (=foreign) genes or genesequences.

It is preferred to employ the compounds (I) according to the inventionin transgenic crops which are resistant to growth regulators such as,for example, dicamba, or against herbicides which inhibit essentialplant enzymes, for example acetolactate synthases (ALS), EPSP synthases,glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD),or against herbicides from the group of the sulfonylureas, glyphosate,glufosinate or benzoylisoxazoles and analogous active ingredients.

When the active ingredients of the invention are used in transgeniccrops, not only do the effects toward harmful plants which are observedin other crops occur, but often also effects which are specific toapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also relates to the use of the compounds of theformula (I) according to the invention and/or their salts as herbicidesfor controlling harmful plants in crops of useful plants or ornamentals,optionally in transgenic crop plants.

Preference is given to the use in cereals, here preferably maize, wheat,barley, rye, oats, millet or rice, by the pre- or post-emergence method.

Preference is also given to the use in soy beans by the pre- orpost-emergence method.

The use according to the invention for the control of harmful plants orfor growth regulation of plants also includes the case in which theactive ingredient of the formula (I) or its salt is not formed from aprecursor substance (“prodrug”) until after application on the plant, inthe plant or in the soil.

The invention also provides the use of one or more compounds of theformula (I) or salts thereof or of a composition according to theinvention (as defined below) (in a method) for controlling harmfulplants or for regulating the growth of plants which comprises applyingan effective amount of one or more compounds of the formula (I) or saltsthereof onto the plants (harmful plants, if appropriate together withthe useful plants), plant seeds, the soil in which or on which theplants grow or the area under cultivation.

The invention also provides a herbicidal or plant growth-regulatingcomposition, characterized in that the composition

(a) comprises one or more compounds of the formula (I) and/or saltsthereof as defined above, preferably one or more compounds of theformula (Ia) and/or salts thereof, in each case as defined above,

and

(b) one or more further substances selected from groups (i) and/or (ii):

-   -   (i) one or more further agrochemically active substances,        preferably selected from the group consisting of insecticides,        acaricides, nematicides, further herbicides (i.e. those not        corresponding to the formula (I) defined above), fungicides,        safeners, fertilizers and/or further growth regulators,    -   (ii) one or more formulation auxiliaries customary in crop        protection.

A herbicidal or plant growth-regulating composition according to theinvention comprises preferably one, two, three or more formulationauxiliaries (ii) customary in crop protection selected from the groupconsisting of surfactants, emulsifiers, dispersants, film-formers,thickeners, inorganic salts, dusting agents, carriers solid at 25° C.and 1013 mbar, preferably absorbant granulated inert materials, wettingagents, antioxidants, stabilizers, buffer substances, antifoam agents,water, organic solvents, preferably organic solvents miscible with waterin any ratio at 25° C. and 1013 mbar.

The compounds (I) according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise compounds of the formula (I) and/or saltsthereof.

The compounds of the formula (I) and/or salts thereof can be formulatedin various ways according to which biological and/or physicochemicalparameters are required. Possible formulations include, for example:Wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates, emulsifiable concentrates (EC), emulsions (EW), such asoil-in-water and water-in-oil emulsions, sprayable solutions, suspensionconcentrates (SC), dispersions based on oil or water, oil-misciblesolutions, capsule suspensions (CS), dusting products (DP), dressings,granules for scattering and soil application, granules (GR) in the formof microgranules, spray granules, absorption and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types and the formulation assistants, suchas inert materials, surfactants, solvents and further additives, areknown to the person skilled in the art and are described, for example,in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nded., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to ClayColloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden,“Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's“Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.;Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ.Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte”[Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft,Stuttgart 1976; Winnacker-Küchler, “Chemische Technologic” [ChemicalTechnology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Wettable powders are preparations which can be dispersed uniformly inwater and, in addition to the active ingredient, apart from a diluent orinert substance, also comprise surfactants of the ionic and/or nonionictype (wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. Toproduce the wettable powders, the herbicidally active ingredients arefinely ground, for example in customary apparatuses such as hammermills, blower mills and air jet mills, and simultaneously orsubsequently mixed with the formulation auxiliaries.

Emulsifiable concentrates are produced by dissolving the activeingredient in an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene, or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more ionic and/or nonionic surfactants (emulsifiers). Examples ofemulsifiers which may be used are: calcium alkylarylsulfonates such ascalcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fattyacid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dustable powders are obtained by grinding the active ingredient withfinely distributed solid substances, for example talc, natural clayssuch as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet-grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be produced, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants as already listedabove, for example, for the other formulation types.

Granules can be prepared either by spraying the active ingredient ontoadsorptive granular inert material or by applying active ingredientconcentrates to the surface of carriers, such as sand, kaolinites orgranular inert material, by means of adhesives, for example polyvinylalcohol, sodium polyacrylate or else mineral oils. Suitable activeingredients can also be granulated in the manner customary for theproduction of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan, fluidized-bed, extruder and spray granules,see e.g. processes in “Spray Drying Handbook” 3rd Ed. 1979, G. GoodwinLtd., London, J. E. Browning, “Agglomeration”, Chemical and Engineering1967, pages 147 ff, “Perry's Chemical Engineer's Handbook”, 5th Ed.,McGraw Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations, preferably herbicidal or plantgrowth-regulating compositions, of the present invention preferablycomprise a total amount of from 0.1 to 99% by weight, preferably 0.5 to95% by weight, particularly preferably 1 to 90% by weight, especiallypreferably 2 to 80% by weight, of active ingredients of the formula (I)and their salts.

In wettable powders, the active ingredient concentration is, forexample, about 10% to 90% by weight, the remainder to 100% by weightconsisting of customary formulation constituents. In emulsifiableconcentrates, the active ingredient concentration may be about 1% to 90%and preferably 5% to 80% by weight. Formulations in the form of dustscomprise 1% to 30% by weight of active ingredient, preferably usually 5%to 20% by weight of active ingredient; sprayable solutions contain about0.05% to 80% by weight, preferably 2% to 50% by weight of activeingredient. In the case of water-dispersible granules, the activeingredient content depends partially on whether the active compound ispresent in liquid or solid form and on which granulation auxiliaries,fillers, etc., are used. In the water-dispersible granules, the contentof active ingredient is, for example, between 1% and 95% by weight,preferably between 10% and 80% by weight.

In addition, the active ingredient formulations mentioned optionallycomprise the respective customary stickers, wetters, dispersants,emulsifiers, penetrants, preservatives, antifreeze agents and solvents,fillers, carriers and dyes, defoamers, evaporation inhibitors and agentswhich influence the pH and the viscosity. Examples of formulationauxiliaries are described inter alia in “Chemistry and Technology ofAgrochemical Formulations”, ed. D. A. Knowles, Kluwer AcademicPublishers (1998).

The compounds of the formula (I) or salts thereof can be employed assuch or in the form of their preparations (formulations) combined withother pesticidally active compounds, such as, for example, insecticides,acaricides, nematicides, herbicides, fungicides, safeners, fertilizersand/or growth regulators, for example as finished formulation or as tankmixes. The combination formulations can be prepared on the basis of theabovementioned formulations, while taking account of the physicalproperties and stabilities of the active ingredients to be combined.

Active ingredients which can be employed in combination with thecompounds of formula (I) according to the invention in mixtureformulations or in a tank mix are, for example, known active ingredientsbased on inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoendesaturase, photosystem I, photosystem II, protoporphyrinogenoxidase, as described, for example, in Weed Research 26 (1986) 441-445or “The Pesticide Manual”, 16th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 2012 and literature citedtherein.

Of particular interest is the selective control of harmful plants incrops of useful plants and ornamentals. Although the compounds (I)according to the invention have already demonstrated very good toadequate selectivity in a large number of crops, in principle, in somecrops and in particular also in the case of mixtures with other, lessselective herbicides, phytotoxicities on the crop plants may occur. Inthis connection, combinations of compounds (I) according to theinvention are of particular interest which comprise the compounds (I) ortheir combinations with other herbicides or pesticides and safeners. Thesafeners, which are used in an antidotically effective amount, reducethe phytotoxic side effects of the herbicides/pesticides employed, forexample in economically important crops, such as cereals (wheat, barley,rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton andsoybeans, preferably cereals.

The weight ratios of herbicide (mixture) to safener depend generally onthe herbicide application rate and the efficacy of the safener inquestion and may vary within wide limits, for example in the range from200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20.Analogously to the compounds (I) or mixtures thereof, the safeners canbe formulated with further herbicides/pesticides and be provided andemployed as a finished formulation or tank mix with the herbicides.

For application, the herbicide or herbicide/safener formulations presentin commercial form are, if appropriate, diluted in a customary manner,for example in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules with water. Dust-typepreparations, granules for soil application or granules for scatteringand sprayable solutions are not normally diluted further with otherinert substances prior to application.

The application rate of the compounds of the formula (I) and/or theirsalts is affected to a certain extent by external conditions such astemperature, humidity, etc. Here, the application rate may vary withinwide limits. For the application as a herbicide for controlling harmfulplants, the total amount of compounds of the formula (I) and their saltsis preferably in the range from 0.001 to 10.0 kg/ha, with preference inthe range from 0.005 to 5 kg/ha, more preferably in the range from 0.01to 1.5 kg/ha, in particular in the range from 0.05 to 1 kg/ha. Thisapplies both to application by the pre-emergence method and thepost-emergence method, the pre-emergence treatment being preferred byvirtue of the significantly higher activity.

When the compounds of the formula (I) and/or their salts are used asplant growth regulator, for example as culm stabilizer for crop plantslike those mentioned above, preferably cereal plants, such as wheat,barley, rye, triticale, millet, rice or maize, the total applicationrate is preferably in the range of from 0.001 to 2 kg/ha, preferably inthe range of from 0.005 to 1 kg/ha, in particular in the range of from10 to 500 g/ha, very particularly in the range from 20 to 250 g/ha. Thisapplies both to the pre-emergence and the post-emergence application.

The application as culm stabilizer may take place at various stages ofthe growth of the plants. Preferred is, for example, the applicationafter the tillering phase, at the beginning of the longitudinal growth.

As an alternative, application as plant growth regulator is alsopossible by treating the seed, which includes various techniques fordressing and coating seed. Here, the application rate depends on theparticular techniques and can be determined in preliminary tests.

EXAMPLE SECTION

Abbreviations and Designations

The symbols “>” and “<” mean “greater than” and “smaller than”,respectively. The symbol “≥” means “greater than or equal to”, thesymbol “≤” means “smaller than or equal to”.

If, in the context of the description and the examples, the designations“R” and “S” are stated for the absolute configuration at a center ofchirality of the stereoisomers of the formulae (I) and (Ia), thisfollows the RS nomenclature of the Cahn-Ingold-Prelog rules.

Abbreviations and designations used:

-   -   Ex.=Example number    -   H=hydrogen (atom)    -   Me=methyl    -   Et=ethyl    -   n-Pr=n-propyl    -   i-Pr=isopropyl    -   n-Bu=n-butyl    -   i-Bu=isobutyl    -   F, Cl, Br, I=fluorine, chlorine, bromine and iodine,        respectively, in accordance with the conventional chemical atom        symbols    -   MeO or OMe=methoxy    -   CN=cyano    -   NO₂=nitro

The position of a substituent at a (phenyl) ring, for example inposition 2 or position 3, is stated as a prefix to the symbol or theabbreviation of the radical, for example

-   -   2-Cl=2-chloro    -   2-Me=2-methyl    -   3-NO₂=3-nitro

Numerations of the substituent positions for di- or trisubstitutedsubstitution patterns are analogously stated as a prefix, for example

-   -   2,3,6-F₃ or 2,3,6-F3=2,3,6-trifluoro (e.g. as substitution at        the phenyl ring)    -   2,3-F₂ or 2,3-F2=2,3-difluoro (e.g. as substitution at the        phenyl ring)

Other abbreviations are to be understood analogously to the examplesstated above.

-   -   “(R²)_(n)=“H”=unsubstituted heteroaromatic radical Q (n=0)    -   “(R³)_(m)=“H”=unsubstituted phenyl ring (m=0)

In addition, the customary chemical symbols and formulae apply, such as,for example, CH₂ for methylene or CF₃ for trifluoromethyl or OH forhydroxyl. Correspondingly, composite meanings are defined as composed ofthe abbreviations mentioned.

In an exemplary manner, some synthesis examples of compounds of theformula (I) are described below. In the examples, the amounts (includingthe percentages) refer to the weight, unless stated otherwise.

Synthesis Examples 1a) Preparation of methyl4-(3-bromo-4-fluorophenyl)-4-cyano-3-(3,5-difluoropyridin-4-yl)butanoate

Under protective gas (argon), 46 mg (0.41 mmol) of potassiumtert-butoxide were added to 0.413 g (2.07 mmol) of methyl(2E)-3-(3,5-difluoropyridin-4-yl)acrylate and 0.443 g (2.07 mmol) of(3-bromo-4-fluorophenyl)acetonitrile in 21.0 ml of toluene and 1 ml ofDMF, and the mixture was stirred at 60° C. for 5 h. After removal of thesolvent under reduced pressure, the residue was taken up in ethylacetate and washed twice with in each case 50 ml of water. The combinedorganic phases were dried over sodium sulfate and the solvent wasremoved under reduced pressure. Chromatography of the residue oversilica gel (ethyl acetate/heptane=15:85) gave 0.501 g (58% of theory) ofthe diastereomeric methyl4-(3-bromo-4-fluorophenyl)-4-cyano-3-(3,5-difluoropyridin-4-yl)butanoates

1b) Preparation of2-(3-bromo-4-fluorophenyl)-3-(3,5-difluoropyridin-4-yl)-5-hydroxypentane-nitrile

Under protective gas (argon), 0.480 g (1.16 mmol) of the methyl4-(3-bromo-4-fluorophenyl)-4-cyano-3-(3,5-difluoropyridin-4-yl)butanoateobtained in step 1a) in 3 ml of THF were added to 0.125 g (2.32 mmol) ofpotassium borohydride and 0.049 g (1.16 mmol) of lithium chloride in 2ml of THF, and the mixture was stirred at 70° C. for 5 h. After coolingto 0° C., water was added. The residue was then taken up in ethylacetate and washed twice with in each case 50 ml of water. The combinedorganic phases were dried over sodium sulfate and the solvent wasremoved under reduced pressure. Chromatography of the residue oversilica gel (ethyl acetate/heptane=15:85) gave 73 mg (16% of theory) ofthe diastereomeric2-(3-bromo-4-fluorophenyl)-3-(3,5-difluoropyridin-4-yl)-5-hydroxypentanenitriles(erythro:threo=49:51, comparison of the doublet in ¹H-NMR in CDCl₃ at4.24 and 4.16 ppm).

1c) Preparation of methyl4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate

Under protective gas (argon), 125 mg (1.11 mmol) of potassiumtert-butoxide were added to 1.006 g (5.55 mmol) of methyl(2E)-3-(5-fluoropyridin-3-yl)acrylate and 0.850 g (5.55 mmol) of(3,4-difluorophenyl)acetonitrile in 45.0 ml of toluene and 2 ml of DMF,and the mixture was stirred at 60° C. for 5 h. After removal of thesolvent under reduced pressure, the residue was taken up in ethylacetate and washed twice with in each case 50 ml of water. The combinedorganic phases were dried over sodium sulfate and the solvent wasremoved under reduced pressure. Chromatography of the residue oversilica gel (ethyl acetate/heptane=15:85) gave 1.050 g (57% of theory) ofthe diastereomeric methyl4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoates.

1d) Preparation of2-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)-5-hydroxypentanenitrile

Under protective gas (argon), 1.050 g (3.14 mmol) of the methyl4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoateobtained in step 1c) in 5 ml THF were added to 0.339 g (6.28 mmol) ofpotassium borohydride and 0.133 g (3.14 mmol) of lithium chloride in 10ml of THF, and the mixture was stirred at 70° C. for 5 h. After coolingto 0° C., water was added. The residue was then taken up in ethylacetate and washed twice with in each case 50 ml of water. The combinedorganic phases were dried over sodium sulfate and the solvent wasremoved under reduced pressure. Chromatography of the residue oversilica gel (ethyl acetate/heptane=15:85) gave 330 mg (35% of theory) ofthe diastereomeric2-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)-5-hydroxypentanenitriles(erythro:threo=59:41, comparison of the doublet in ¹H-NMR in CDCl₃ at4.29 and 4.04 ppm).

1e) Preparation of(2R,3R)-2-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)-5-hydroxypentanenitrile

Preparative chromatography [(80 ml/min n-heptane/2-propanol (80:20)] of100 mg of the diastereomer mixture obtained as above in step 1d)(dissolved in 4.0 ml of methanol) on a chiral stationary phase[Chiralpak IC, 20 μm, (250×50) mm column] gave 19 mg of(2R,3R)-2-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)-5-hydroxypentanenitrilewhich eluted as the penultimate of the four stereoisomers (retentiontime: 11.9 min). The absolute configuration of this compound wassubsequently assigned by X-ray structure analysis.

1f) Preparation of4-(3-bromo-4-fluorophenyl)-4-cyano-3-(3,5-difluoropyridin-4-yl)butylchloroacetate

Under protective gas (argon), 21 mg (0.18 mmol) of chloroacetyl chloridewere added to 35 mg (0.09 mmol) of2-(3-bromo-4-fluorophenyl)-3-(3,5-difluoropyridin-4-yl)-5-hydroxypentanenitrile(obtained in step 1b) above), 4-(dimethylamino)pyridine 7 mg (0.05 mmol)and 18 mg (0.18 mmol) of triethylamine in 3 ml of dichloromethane, andthe mixture was stirred at 25° C. for 3 h. The residue was taken up inethyl acetate and washed twice with in each case 50 ml of water. Thecombined organic phases were then dried over sodium sulfate and thesolvent was removed under reduced pressure. Chromatography of theresidue over silica gel (ethyl acetate/heptane=15:85) gave 17 mg (41% oftheory) of the diastereomeric4-(3-bromo-4-fluorophenyl)-4-cyano-3-(3,5-difluoropyridin-4-yl)butylchloroacetates (erythro:threo=48:52, comparison of the singlets in¹H-NMR in CDCl₃ at 8.42 and 8.25 ppm).

Definition and Description of Preferred Compounds According to theInvention—Analytical and Physical Data

Compounds of the formula (I) according to the invention havingcorresponding individual numbers (=example numbers) are listed below,where the respective compound name is composed of the compound number ofthe chemical formula (I) which refers to the same number as given in therespective line of the table, i.e. the structure combination of groupsQ(R²)_(n) and (R³)_(m) is defined according to the correspondingconsecutive entry number (hereinbelow “line number”, without countingthe header of table 1) of table 1.

In this manner, the respective chemical structure of a compound of theformula (I) according to the invention is defined unambiguously, whichis demonstrated using the following examples:

The compound name “215a” identifies the compound of the formula (Ia)[corresponds to formula (I) in which R¹═H (=hydrogen)] in whichQ(R²)_(n)=3-chloropyridin-2-yl and (R³)_(m)=3-Cl, 4-F according to linenumber 215 of table 1.

The compound name “296a” identifies the compound of the formula (Ia)[corresponds to formula (I) in which R¹═H (=hydrogen)] in whichQ(R²)_(n)=5-fluoropyridin-3-yl and (R³)_(m)=3-Cl, 4-F according to linenumber 296 of table 1.

The compound name “599a” identifies the compound of the formula (Ia)[corresponds to formula (I) in which R¹═H (=hydrogen)] in whichQ(R²)_(n)=3,5-difluoropyridin-4-yl and (R³)_(m)=3-Cl according to linenumber 599 of table 1.

The compound name “1295a” identifies the compound of the formula (Ia)[corresponds to formula (I) in which R¹═H (=hydrogen)] in whichQ(R²)_(n)=5-chloropyrazin-2-yl and (R³)_(m)=3-Cl, 4-F according to linenumber 1295 of table 1.

The compound name “1477a” identifies the compound of the formula (Ia)[corresponds to formula (I) in which R¹═H (=hydrogen)] in whichQ(R²)_(n)=4-chloro-2-thienyl and (R³)_(m)=3,4-F₂ according to linenumber 1477 of table 1.

Definitions of R¹ in preferred compounds of the formula (I) according tothe invention are listed in table U1 below.

TABLE U1 Formula R¹ in formula (I) (Ia) H (hydrogen) (Ibb) acetyl (Ibc)propanoyl (Ibd) butanoyl (Ibe) 2-methylpropanoyl (= isopropanoyl) (Ibf)2,2-difluoroacetyl (Ibg) 2,2,2-trifluoroacetyl (Ibh) C(O)OMe (Ibi)cyclopropanecarbonyl (Ibj) 1-methylcyclopropanecarbonyl (Ibk) acryl(Ibl) prop-2-ynoyl (Ibm) but-2-ynoyl (Ibn) 2-methylacryl (Ibo) benzoyl(Ibp) 4-chlorobenzoyl (Ibq) 3-chlorobenzoyl (Ibr) 2-chlorobenzoyl (Ibs)4-fluorobenzoyl (Ibt) 3-fluorobenzoyl (Ibu) 2-fluorobenzoyl (Ibv)2,2-dimethylpropanoyl (= pivaloyl) (Ibw) 3,3-dimethylbutanoyl (Ibx)pentanoyl (Iby) hexanoyl (Ibz) 2-nitrobenzoyl (Ibaa) 2-fluoroacetyl(Ibab) 2-chloroacetyl (Ibac) 2-bromoacetyl (Ibad) 2,2-dichloroacetyl(Ibae) 2-methoxyacetyl (Ibaf) 2,6-difluorobenzoyl (Ibag) C(O)C(O)OMe(Ibah) C(O)CH₂C(O)OMe

Examples of compounds of the formulae (Ia) and (Ibb) to (Ibah) accordingto the invention are the compounds of the relevant formulae (Ia) and(Ibb) to (Ibah) according to table U1 above in which the structurecombination of groups Q(R²)_(n) and (R³)_(m) is defined by a line numberof table 1.

Thus, for example, the compound name “619bab” identifies the compound ofthe formula (I) in which R¹=2-chloroacetyl andQ(R²)_(n)=3,5-difluoropyridin-4-yl and (R³)_(m)=3-Br, 4-F according toline number 619 of table 1.

The compound name “599bae” identifies the compound of the formula (I) inwhich R¹=2-methoxy-acetyl and Q(R²)_(n)=3,5-difluoropyridin-4-yl and(R³)_(m)=3-Cl according to line number 599 of table 1.

These compounds may be present, for example, in the form of anerythro/threo mixture in a quantitative ratio of 70:30 to 30:70, forexample in the form of a racemic erythro/threo mixture.

Information regarding the examples given in Tables 2a to 2d:

In Tables 2a to 2d below, the compounds according to the invention areassigned corresponding individual numbers (=example numbers), where theparticular example number is composed of the compound number of thechemical formula (I), which refers to the same number as given in therespective line of the table, followed by the respective stereoisomericform. The particular stereoisomeric form corresponds to theabove-defined formulae (I threo-1), (I threo-2), (I erythro-1) and (Ierythro-2), or mixtures of these stereoisomers.

The same applies to the assignment of racemic or optically active threostereoisomers or erythro stereoisomers of the compounds according to theinvention.

In this way, the stereoisomers are given the respective clearly definedchemical structure of a compound of the formula (I) according to theinvention, which the following examples aim to illustrate:

The compound name “208a threo” identifies a mixture of the “threo”isomers of the compound of the formula (I), in which R¹═H (=hydrogen),and Q(R²)_(n)=3-chloropyridin-2-yl and (R³)_(m)=3,4-F₂ according to linenumber 208 from Table 1.

The compound name “532a erythro” identifies a mixture of the “erythro”isomers of the compound of the formula (I) in which R¹═H (=hydrogen),and Q(R²)_(n)=2-chloropyridin-4-yl and (R³)_(m)=3,4-F₂ according to linenumber 532 from Table 1.

The compound name “289a threo-2” identifies the “threo-2” isomers of thecompound of the formula (I) [corresponding to formula (I threo-2)], inwhich R¹═H (=hydrogen), and Q(R²)_(n)=5-fluoropyridin-3-yl and(R³)_(m)=3,4-F₂ according to entry number 289 from Table 1.

The compound name “532a erythro-1” identifies the “erythro-1” isomers ofthe compound of the formula (I) [corresponding to formula (Ierythro-1)], in which R¹═H (=hydrogen), andQ(R²)_(n)=2-chloropyridin-4-yl and (R³)_(m)=3,4-F₂ according to linenumber 532 from Table 1.

Tables 2a to 2d: Preferred Compounds of the Formulae (I threo-1), (Ithreo-2), (I erytro-1) and (I erytro-2) According to the Invention

Table 2a: Preferred (I threo-1) Enantiomers

Table 2a describes the compounds of the formulae (1 threo-1) to (1809threo-1), in which the structure combination of the groups Q(R²)_(n) and(R³)_(m) is defined according to a line number from Table 1, asexplained in detail above, R¹ preferably being selected from Table U1and preferably R¹═H (hydrogen).

Table 2b: Preferred (I threo-2) Enantiomers

Table 2b describes the compounds of the formulae (1 threo-2) to (1809threo-2), in which the structure combination of the groups Q(R²)_(n) and(R³)_(m) is defined according to a line number from Table 1, asexplained in detail above, R¹ preferably being selected from Table U1and preferably R¹═H (hydrogen).

Table 2c: Preferred (I erythro-1) Enantiomers

Table 2c describes the compounds of the formulae (1 erythro-1) to (1809erythro-1), in which the structure combination of the groups Q(R²)_(n)and (R³)_(m) is defined according to a line number from Table 1, asexplained in detail above, R¹ preferably being selected from Table U1and preferably R¹═H (hydrogen).

Table 2d: Preferred (I erythro-2) Enantiomers

Table 2d describes the compounds of the formulae (1 erythro-2) to (1809erythro-2), in which the structure combination of the groups Q(R²)_(n)and (R³)_(m) is defined according to a line number from Table 1, asexplained in detail above, R¹ preferably being selected from Table U1and preferably R¹═H (hydrogen).

Physical Data of Some Compounds According to the Invention:

Test Methods:

-   -   1) NMR=¹H-NMR data (400 MHz, CDCl₃); characteristic chemical        shifts [in ppm] are given for the respective example.    -   2) HPLC=High Performance Liquid Chromatography, column: Zorbax        Eclipse, 50×3.0, C18 1.8 μm, mobile phase: water+0.06% formic        acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2        min 5:95; detector: DAD (210-400 nm); retention time (Rt)        indicated for the example in question,    -   3) chiral HPLC=HPLC on a chiral column, column: Chiralpak IC,        250×4.6 mm, 5 μm DAIC 83325, detector wavelength: 210 nm; column        temperature 25° C.,        -   mobile phase a: (n-heptane:2-propanol), (60:40), Chromasolv,            flow rate: 1.0 ml/min        -   mobile phase b: (n-heptane:2-propanol), (70:30), Chromasolv,            flow rate: 1.0 ml/min        -   mobile phase c: (n-heptane:2-propanol), (80:20), Chromasolv,            flow rate: 1.0 ml/min        -   mobile phase d: (n-heptane:2-propanol), (90:10), Chromasolv,            flow rate: 0.6 ml/min

NMR Data of Selected Compounds According to the Invention

¹H-NMR data (CDCl₃)—chemical shift of selected characteristic signals inppm.

NMR Peak List Method

The ¹H-NMR data (also referred to below as 1H-NMR) of selected examplesare noted in the form of 1H-NMR peak lists. For each signal peak, firstthe δ value in ppm and then the signal intensity in round brackets arelisted. The pairs of δ value—signal intensity numbers for differentsignal peaks are listed with separation from one another by semicolons.

The peak list for one example therefore has the form:

δ₁ (intensity₁ ⁾; δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i) ⁾; . . .; δ_(a) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

Calibration of the chemical shift of 1H NMR spectra is accomplishedusing tetramethylsilane and/or the chemical shift of the solvent,particularly in the case of spectra which are measured in DMSO.Therefore, the tetramethylsilane peak may but need not occur in NMR peaklists.

The lists of the 1H-NMR peaks are similar to the classic 1H-NMR printsand thus usually comprise all peaks listed in classic NMRinterpretations.

In addition, like classic 1H-NMR prints, they may show solvent signals,signals of stereoisomers of the target compounds, which are likewisepart of the subject matter of the invention, and/or peaks of impurities.

When stating compound signals in the delta range of solvents and/orwater, in our lists of 1H NMR peaks, the usual solvent peaks, forexample peaks of DMSO in DMSO-D₆ and the peak of water are shown, whichusually have on average a high intensity.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in classical 1H-NMR interpretation.

Further details of 1H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

Compound 215a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.577(10.7); 8.573(11.0);8.565(11.1); 8.562(10.9); 8.524(6.5); 8.520(6.7); 8.512(6.8);8.509(6.5); 7.729(11.1); 7.725(11.2); 7.708(12.4); 7.705(11.8);7.539(8.0); 7.535(7.9); 7.518(15.9); 7.515(8.7); 7.414(8.9); 7.409(9.8);7.398(9.1); 7.392(9.5); 7.359(1.4); 7.292(2.8); 7.260(1373.1);7.251(10.7); 7.245(7.0); 7.239(5.8); 7.235(7.8); 7.227(15.1);7.224(8.3); 7.216(14.9); 7.210(5.7); 7.207(12.2); 7.196(13.8);7.192(6.9); 7.181(6.4); 7.175(6.8); 7.166(13.1); 7.158(1.8);7.145(21.2); 7.124(8.8); 7.115(9.4); 7.103(9.0); 7.094(8.5); 7.083(8.6);7.046(2.6); 7.040(2.5); 7.035(2.9); 7.029(2.6); 7.025(4.6); 7.019(4.5);7.013 (4.6); 7008(4.4); 6.996(8.2); 6.984(8.8); 6.963(12.5); 6.942(4.6);6.914(1.0); 4.362(13.3); 4.357(9.1); 4.338(16.0); 44.332 (10.9);4.163(2.9); 4.144(7.3); 4.133(5.4); 4.128(3.7); 4.120(10.4); 4.109(8.1);4.103(2.9); 4.096(3.7); 4.085(3.6); 3.637(2.4); 3.623(4.6); 3.609(5.6);3.596(6.3); 3.581(3.2); 3.524(3.3); 3.510(6.7); 3.496(7.6); 3.492(4.3);3.482(10.3); 3.476(5.7); 3.468 (5.7); 3.458(3.7); 3.448(3.5);3.430(2.6); 3.415(5.5); 3.401(6.5); 3.395(6.4); 3.387(3.9); 3.382(6.1);3.374(3.9); 3.367(4.2); 3.354(3.6); 2.413(4.9); 2.398(7.4); 2.382(6.8);2.379(8.4); 2.365(4.9); 2.110(1.9); 2.097(3.6); 2.087(2.2); 2.073(4.2);2.062 (5.0); 2.052(2.8); 2.038(4.6); 2.025(2.2); 2.005(2.4); 1.882(2.8);1.870(3.1); 1.866(3.3); 1.862(3.3); 1.855(3.1); 1.851(3.6); 1.847(4.9);1.836(4.7); 1.832(2.8); 1.827(2.8); 1.821(2.6); 1.816(2.5); 1.801(2.0);1.587(6.3); 0.157(2.0); 0.146(1.6); 0.008 (16.7); 0.000(516.3);−0.009(15.4); −0.050(1.6); −0.149(1.6) Compound 1484a: 1H-NMR (400.0MHz. CDCl3): δ = 8.003(1.8); 7.301(2.2); 7.295(2.4); 7.284(2.4);7.279(2.3); 7.263(50.3); 7.220(4.5); 7.214(4.8); 7.203(4.6); 7.197(4.6);7.131 (1.3); 7.110(6.2); 7.089(14.8); 7.083(2.2); 7.077(2.4);7.068(7.4); 7.062(0.8); 7.056(0.6); 7.050(0.6); 7.019(3.1); 7.014 (3.1);7.009(3.5); 7.000(6.4); 6.997(6.9); 6.992(2.2); 6.987(2.1); 6.981(2.0);6.973(11.3); 6.969(11.7); 6.718(14.0); 6.717(14.2); 6.715(14.3);4.190(6.7); 4.176(7.0); 4.010(3.4); 3.993(3.7); 3.813(1.8); 3.801(4.0);3.787(3.7); 3.774(5.2); 3.761(2.5); 3.750 (0.9); 3.741(1.1); 3.736(1.1);3.724(1.4); 3.714(1.3); 3.709(1.3); 3.699(1.1); 3.623(2.4); 3.612(2.7);3.602(2.8); 3.596(2.2); 3.590(2.8); 3.585(2.2); 3.575(2.6); 3.564(2.9);3.556(1.0); 3.546(3.2); 3.532(3.6); 3.522(2.5); 3.517(3.5); 3.508(3.8);3.493 (3.1); 3.484(15.8); 3.479(1.4); 3.466(1.1); 3.454(1.0);2.958(16.0); 2.880(13.6); 2.879(13.4); 2.279(0.5); 2.270(0.6); 2.264(0.6); 2.255(1.1); 2.244(0.9); 2.240(0.6); 2.235(0.48); 2.230(0.9);2.220(1.3); 2.211(0.7); 2.205(0.6); 2.196(0.6); 2.189(0.7); 2.176(1.2);2.168(0.7); 2.163(0.9); 2.154(2.6); 2.141(3.5); 2.133(2.0); 2.127(1.8);2.119(2.9); 2.114(1.8); 2.106(1.9); 2.102 (3.3); 2.090(3.1); 2.078(3.4);2.066(2.6); 2.054(1.2); 2.042(1.2); 2.030(0.6); 2.018(0.6); 2.007(1.0);1.996(0.7); 1.989(0.6); 1.983(0.7); 1.979(1.1); 1.972(0.9); 1.968(0.7);1.954(0.5); 1.944(0.8); 1.496(6.6); 0.008(0.6); 0.000(19.0) Compound181a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.523(3.7); 8.520(1.5); 8.517(1.6);8.513(3.7); 8.481(5.3); 8.472(5.3); 7.263(50.0); 7.259(12.4);7.200(1.1); 7.186(2.3); 7.180(1.4); 7.176(1.6); 7.170(2.8); 7.166(4.8);7.162(5.3); 7.157(5.1); 7.154(4.); 7.147(1.2); 7.086(0.3); 7.063(1.6);7.061 (1.3); 7.057(1.2); 7.046(2.2); 7.032(2.7); 7.016(2.6); 7.002(1.5);6.990(1.4); 6.987(1.5); 6.978(1.5); 6.974(2.0); 6.969(1.5); 6.960 (1.4);6.957(1.4); 6.930(6.1); 6.927(5.8); 6.866(1.9); 6.863(1.6); 6.859(1.5);6.852(1.6); 4.381(4.8); 4.364(5.0); 4.317(3.8); 4.301(3.9); 3.684(1.3);3.677(1.8); 3.675(1.8); 3.667(2.2); 3.658(2.1); 3.657(2.0); 3.649(1.5);3.563(1.0); 3.554(1.7); 3.545 (2.1); 3.536(2.0); 3.527(1.2); 3.488(4.1);3.458(1.0); 3.451(1.1); 3.442(2.0); 3.435(2.4); 3.426(1.3); 3.420(2.9);3.415(2.5); 3.404(1.4); 3.398(1.3); 3.377(1.5); 3.370(1.7); 3.361(2.0);3.359(1.8); 3.354(2.0); 3.352(1.8); 3.343(1.5); 3.336(1.4); 3.330 (1.2);3.322(1.3); 3.315(1.4); 3.312(1.3); 3.307(1.4); 3.304(1.3); 3.297(1.2);3.289(1.0); 2.403(0.6); 2.397(0.7); 2.393(0.7); 2.387(1.2); 2.380(1.3);2.371(1.3); 2.364(1.6); 2.358(1.0); 2.354(0.9); 2.349(0.8); 2.261(0.9);2.254(1.7); 2.246(1.0); 2.243 (1.0); 2.236(1.9); 2.230(1.6); 2.223(0.7);2.220(0.7); 2.213(1.2); 2.205(0.6); 2.001(0.7); 1.994(1.2); 1.985(1.2);1.977(1.7); 1.970(2.0); 1.962(1.7); 1.953(2.1); 1.945(1.7); 1.915(2.2);1.833(0.9); 1.825(1.1); 1.817(1.2); 1.810(1.4); 1.801(1.4); 1.794(0.9);1.787(0.8); 1.778(0.6); 0.005(0.6); 0.000(12.8); −0.006(0.5) Compound1515a: 1H-NMR (400.0 MHz. CDCl3): δ = 7.361(0.5); 7.351(0.7);7.348(1.0); 7.338(2.5); 7.328(2.1); 7.324(3.6); 7.315(3.2); 7.311(2.1);7.301(1.9); 7.291(4.1); 7.262 (50.0); 7.114(12.4); 7.092(0.4);7.085(0.3); 7.072(0.5); 7.068(0.6); 7.058(1.0); 7.052(1.8); 7.047(1.8);7.036(3.3); 7.033(4.1); 7.019(2.6); 7.010(0.8); 7.007(1.0); 6.995(0.48);6.992(1.0); 6.969(3.8); 6.956(3.5); 6.930(2.2); 6.927(3.0); 6.914(2.2);6.911 (2.9); 4.280(5.6); 4.271(5.7); 4.061(1.8); 4.050(1.9); 3.851(1.5);3.843(3.0); 3.834(2.9); 3.825(3.5); 3.816(1.7); 3.761(0.6); 3.755(1.0);3.749(1.1); 3.739(2.5); 3.730(3.8); 3.723(2.5); 3.714(2.9); 3.705(1.4);3.640(1.7); 3.633(1.9); 3.625(2.1); 3.622 (1.9); 3.618(2.1); 3.615(1.8);3.607(1.6); 3.600(1.5); 3.495(0.6); 3.490(2.8); 3.478(0.9); 3.471(0.9);3.460(0.5); 3.453(0.5); 2.259(0.5); 2.252(0.6); 2.243(0.6); 2.236(0.6);2.230(1.0); 2.221(1.4); 2.215(0.9); 2.212(0.9); 2.207(2.1); 2.198(2.3);2.192 (1.3); 2.189(1.2); 2.183(1.7); 2.174(0.9); 2.110(1.0); 2.103(1.7);2.095(1.9); 2.087(2.3); 2.079(2.1); 2.071(1.3); 2.064(1.1); 2.055(0.6);1.939(0.5); 1.932(0.3); 1.928(0.3); 1.921(0.6); 1.916(0.6); 1.897(0.5);1.556(7.6); 0.000(14.4); −0.006(0.5) Compound 1461a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.004(1.0); 7.343(1.1); 7.328(1.4); 7.324(3.8); 7.309(4.0);7.304(5.0); 7.289(4.9); 7.284(3.1); 7.269(3.2); 7.261(50.1); 7.054(0.9); 7.052(1.1); 7.047(1.1); 7.045(1.5); 7.043(1.9); 7.041(2.0);7.036(2.1); 7.034(2.6); 7.031(2.5); 7.027(3.6); 7.024(4.7); 7.022(5.5);7.020(4.4); 7.016(3.6); 7.013(3.8); 7.009(2.2); 7.004(3.9); 7.001(2.8);6.999(2.0); 6.995(1.9); 6.992(2.1); 6.988 (6.3); 6.985(7.2); 6.982(2.3);6.976(1.2); 6.963(2.1); 6.956(15.1); 6.952(16.0); 6.934(3.7);6.933(3.5); 6.904(2.7); 6.899(3.4); 6.893(2.1); 6.880(2.7); 6.875(3.3);6.870(2.1); 6.727(5.1); 6.726(5.0); 6.724(5.1); 6.722(4.8); 6.708(9.2);6.707(9.3); 6.704 (9.4); 4.202(6.9); 4.187(7.2); 4.043(3.7); 4.026(4.0);3.800(1.8); 3.787(3.8); 3.774(3.8); 3.761(4.9); 3.748(2.4); 3.733(1.0);3.724(1.2); 3.719(1.2); 3.707(1.7); 3.697(1.5); 3.692(1.4); 3.682(1.2);3.614(2.4); 3.603(2.7); 3.593(3.6); 3.587(2.5); 3.581 (4.9); 3.576(3.3);3.566(6.3); 3.554(4.4); 3.543(3.5); 3.528(1.7); 3.508(1.3); 3.496(1.5);3.484(10.9); 3.472(1.6); 3.469(1.4); 3.457(1.2); 3.445(1.1); 2.956(9.3);2.879(7.8); 2.878(7.6); 2.281(0.6); 2.272(0.6); 2.266(0.6); 2.258(1.2);2.247(0.9); 2.243 (0.7); 2.238(0.8); 2.232(0.9); 2.223(1.5); 2.214(0.8);2.208(0.7); 2.199(0.7); 2.187(0.7); 2.174(1.3); 2.166(0.7); 2.161(0.9);2.152(2.7); 2.139(3.7); 2.131(2.0); 2.125(1.8); 2.118(3.2); 2.111(1.8);2.104(1.8); 2.099(3.4); 2.087(3.0); 2.075(3.4); 2.063 (2.5); 2.052(1.2);2.039(1.8); 2.028(1.6); 2.017(0.7); 2.010(0.7); 2.004(07); 2.000(1.0);1.993(0.9); 1.989(0.8); 1.982(0.5); 1.976(0.6); 1.965(0.7); 1.954(0.5);1.449(4.9); 0.008(0.6); 0.000(19.6); −0.009(0.5) Compound 1677a: 1H-NMR(400.0 MHz. CDCl3): δ = 8.001(1.8); 7.334(1.9); 7.327(3.8); 7.319(2.2);7.312(5.7); 7.306(6.6); 7.300(4.3); 7.292(6.9); 7.286(5.1); 7.279(2.8);7.272 (5.1); 7.262(65.8); 7.043(1.6); 7.040(4.0); 7.037(4.2);7.034(4.5); 7.031(3.7); 7.019(9.5); 7.016(8.0); 7.013(7.7); 7.010(6.5);7.007(2.8); 7.006(2.9); 7.005(3.1); 7.003(3.7); 7.001(4.5); 6.999(4.0);6.998(4.2); 6.995(4.0); 6.992(3.7); 6.989(3.0); 6.978 (4.9); 6.977(5.7);6.974(9.2); 6.971(6.4); 6.964(2.2); 6.958(4.9); 6.957(5.1); 6.955(6.4);6.954(6.1); 6.953(5.9); 6.952(6.1); 6.946(3.0); 6.940(1.8); 6.915(4.5);6.910(5.5); 6.905(3.5); 6.892(4.5); 6.886(5.5); 6.881(3.5); 6.394(3.5);6.393(3.5); 6.385 (7.2); 6.383(5.0); 6.380(7.1); 6.378(7.3); 6.376(5.3);6.375(5.0); 6.370(13.2); 6.362(7.7); 6.360(7.3); 6.266(12.9);6.261(13.1); 6.256(11.0) 6.251(12.0); 6.250(8.3); 6.245(6.7);6.240(5.47); 6.236(5.6); 4.150(11.5); 4.136(12.0); 3.992(6.1);3.974(6.5); 3.803(3.0); 3.790(6.3); 3.776(6.6); 3.763(8.5); 3.750(5.6);3.741(1.9); 3.736(1.9); 3.724(2.7); 3.714(2.4); 3.709(2.3); 3.699 (2.1);3.641(4.2); 3.629(4.7); 3.620(4.9); 3.614(3.6); 3.608(4.43.602(3.5);3.593(3.6); 3.581(3.3); 3.549(2.2); 3.537(2.5); 3.526(2.6); 3.522(2.1);3.514(2.6); 3.510(2.2); 3.499(2.0); 3.487(1.9); 3.481(6.3); 3.467(1.9);3.461(2.6); 3.452(4.1); 3.446 (4.0); 3.443(3.6); 3.437(3.2); 3.433(3.2);3.428(3.5); 3.422(3.7); 3.414(1.8); 3.408(1.5); 2.956(16.0);2.878(14.1); 2.877(14.0); 2.276(0.9); 2.267(0.9); 2.261(1.0);2.252(1.8); 2.243(1.2); 2.241(1.4); 2.238(1.1); 2.232(1.3); 2.229(1.2);2.226(1.4); 2.218 (2.42.209(1.2); 2.203(1.1); 2.194(1.0); 2.142(1.1);2.129(2.3); 2.121(1.2); 2.116(1.4); 2.107(4.5); 2.094(6.2); 2.086(3.3);2.080(2.9); 2.072(5.4); 2.064(3.1); 2.059(2.9); 2.052(5.8); 2.040(5.3);2.028(5.7); 2.016(3.7); 2.004(2.2); 1.992(2.3); 1.980 (1.1); 1 972(1.1);1 960(1.6); 1.950(1.2); 1 943(1.1); 1 937(1.1); 1.932(1.6); 1 925(1.4);1.921(1.2); 1.915(0.9); 1.908(0.9); 1.898 (1.2); 1.886(0.8);1.498(12.3); 0.008(0.7); 0.000(25.4); −0.009(0.7) Compound 1153a: 1H-NMR(400.0 MHz. CDCl3): δ = 8.095(2.9); 8.090(5.8); 8.087(3.3); 8.082(5.6);7.264(29.0); 7.127(1.4); 7.119(0.9); 7.113(3.1); 7.105(1.7); 7.097(3.0); 7.089(1.6); 7.083(1.6); 7.075(0.7); 7.065(0.7); 7.061(0.7);7.053(0.8); 7.048(1.1); 7.043(0.8); 7.035(0.7); 7.031(0.7); 7.013(1.5);7.010(1.6); 7.001(1.7); 6.997(2.3); 6.992(1.7); 6.984(1.5); 6.980(1.5);6.914(1.0); 6.907(0.8); 6.900(0.9); 6.886 (2.2); 6.879(1.7); 6.871(1.9);6.666(2.1); 6.664(2.4); 6.658(5.6); 6.652(4.2); 6.650(3.9); 6.499(3.5);6.476(7.7); 4.192(5.3); 4.181(5.3); 4.031(0.4); 3.987(2.4); 3.974(2.5);3.912(50.0); 3.724(1.4); 3.715(2.9); 3.706(3.0); 3.698(3.43.689(1.6);3.659 (0.6); 3.652(0.8); 3.649(0.8); 3.642(1.3); 3.634(0.9); 3.631(0.9);3.624(0.7); 3.494(1.7); 3.488(3.2); 3.480(1.9); 3.476(1.7); 3.471(1.9);3.468(1.7); 3.462(1.5); 3.454(1.4); 3.381(0.43.373(0.7); 3.365(1.0);3.357(1.0); 3.348(0.7); 3.340(0.6); 3.278 (0.7); 3.268(1.6); 3.259(3.3);3.253(2.3); 3.248(2.2); 3.242(2.8); 3.232(1.3); 2.272(0.3); 2.266(0.4);2.262(0.4); 2.256(0.7); 2.249(0.7); 2.240(0.7); 2.233(0.8); 2.227(0.5);2.223(0.4); 2.217(0.4); 2.110(0.6); 2.101(1.1); 2.096(0.8); 2.091(1.1);2.087 (2.4); 2.077(3.6); 2.070(3.8); 2.063(6.4); 2.054(6.4); 2.046(6.1);2.038(4.2); 2.031(2.1); 2.022(2.0); 2.014(1.1); 0.000(8.3) Compound 532athreo: 1H-NMR (400.0 MHz. CDCl3): δ = 8.341(15.5); 8.339(15.4);8.328(16.0); 8.326(15.5); 8.308(0.8); 7.519(4.8); 7.379(0.6);7.310(1.0); 7.293(1.7); 7.260(903.9); 7.229(0.7); 7.210(1.3);7.163(5.1); 7.142(8.1); 7.138(6.3); 7.121(7.6); 7.116(20.9);7.112(19.5); 7.102(5.3); 7.097(10.7); 7.084(5.1); 7.078(5.8);7.070(5.1); 7.058(4.8); 7.052(4.9); 7.032(12.4); 7.028(11.3);7.018(11.4); 7.015(10.7); 6.996(5.2); 6.975(0.8); 6.918(3.2);6.913(4.0); 6.909(5.6); 6.904(4.3); 6.898(4.3); 6.892(3.7); 6.887(4.7);6.883(3.3); 6.877(2.4); 5.299 (4.5); 4.032(13.8); 4.014(14.6);3.709(2.1); 3.696(3.1); 3.683(4.1); 3.672(3.6); 3.658(2.6); 3.384(4.7);3.374(5.3); 3.366(5.1); 3.356(10.5); 3.346(7.1); 3.338(5.6); 3.328(5.2);2.288(2.0); 2.278(2.2); 2.273(2.4); 2.263(4.3); 2.252(4.3); 2.242(3.4);2.238 (4.3); 2.228(5.8); 2.218(3.2); 2.214(3.0); 2.204(2.6); 2.170(0.6);2.088(2.8); 2.077(5.2); 2.067(3.0); 2.061(2.7); 2.050(5.2); 2.042(4.5);2.031(2.0); 2.025(2.2); 2.014(3.4); 2.004(1.9); 1.541(60.1); 1.333(3.2);1.284(6.3); 1.256(5.0); 0.880(0.8); 0.146 (1.0); 0.008(9.2);0.000(342.5); −0.006(4.9); −0.009(11.0); −0.051(0.6); −0.150(1.1)Compound 1288a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.620(14.8); 8.617(14.8);8.565(12.7); 8.562(12.6); 8.189(16.0); 8.185(15.7); 8.010(0.7);7.963(13.47.960 (13.4); 7.520(1.1); 7.261(212.1); 7.215(2.8);7.211(0.6); 7.195(5.3); 7.191(3.5); 7.180(3.4); 7.174(7.3); 7.170(5.7);7.162 (3.3); 7.154(4.1); 7.149(5.2); 7.135(3.0); 7.129(3.1); 7.077(2.7);7.056(4.8); 7.053(3.7); 7.046(3.1); 7.041(4.3); 7.036(6.4); 7.032(6.8);7.023(4.7); 7.017(4.5); 7.011(4.5); 7.005(2.9); 6.997(4.1); 6.991(2.8);6.978(2.5); 6.973(2.6); 6.860(1.8); 6.856 (2.2); 6.851(3.2); 6.846(2.3);6.840(2.2); 6.835(2.0); 6.829(2.5); 6.825(1.8); 6.820(1.3); 4.292(9.2);4.285(8.4); 4.270(9.6); 4.260 (8.7); 3.728(2.0); 3.717(2.8); 3.701(2.9);3.690(3.2); 3.676(2.3); 3.645(2.3); 3.633(4.5); 3.619(4.6); 3.605(6.3);3.594(6.0); 3.583(3.3); 3.577(4.0); 3.570(6.1); 3.561(3.6); 3.552(2.9);3.548(3.1); 3.543(2.5); 3.536(2.5); 3.346(2.43.335(3.0); 3.323 (5.3);3.319(3.3); 3.312(5.8); 3.308(3.2); 3.297(5.0); 3.286(4.9); 3.272(2.3);3.261(2.1); 2.958(5.6); 2.882(4.8); 2.489(1.1); 2.480(1.2); 2.475(1.2);2.466(1.8); 2.454(2.0); 2.441(1.8); 2.431(2.2); 2.422(1.4); 2.417(1.3);2.408(1.1); 2.236(1.3); 2.225 (2.7); 2.215(1.5); 2.209(1.4); 2.198(2.9);2.191(2.4); 2.180(1.1); 2.174(1.1); 2.163(2.0); 2.153(0.9); 2.063(1.0);2.052(1.9); 2.040(1.5); 2.028(3.0); 2.017(3.8); 2.004(2.8); 1.992(3.3);1.980(1.6); 1.960(1.7); 1.948(2.9); 1.935(2.4); 1.925(3.6); 1.913 (3.1);1.902(1.3); 1.890(1.5); 1.878(0.9); 1.485(1.6); 0.008(2.6); 0.000(79.4);−0.009(2.3) Compound 1477a: 1H-NMR (400.0 MHz. CDCl3): δ =8.003(1.47.262(60.8); 7.166(1.4); 7.152(2.8); 7.145(2.5); 7.142(1.8);7.131(4.7); 7.127(3.4); 7.121(2.6); 7.111(3.5); 7.106 (4.6); 7.100(2.0);7.097(1.6); 7.091(1.6); 7.086(3.2); 7.079(1.4); 7.073(1.6); 7.071(1.5);7.065(1.4); 7.052(1.3); 7.046(1.4); 7.016(2.3); 7.010(2.5); 6.997(3.0);6.994(7.3); 6.991(9.2); 6.983(2.8); 6.971(2.9); 6.966(15.2);6.962(14.1); 6.958(2.2); 6.954(1.4); 6.947(1.2); 6.941(1.0); 6.936(1.3);6.931(1.0); 6.927(0.7); 6.903(1.7); 6.899(2.1); 6.894(2.9); 6.889(2.2);6.883 (2.2); 6.878(1.8); 6.873(2.3); 6.868(1.7); 6.863(1.2);6.722(10.6); 6.721(11.5); 6.719(11.3); 6.718(11.0); 6.715(6.8);6.714(6.4); 6.711(6.2); 6.710(5.8); 4.199(7.1); 4.185(7.4); 4.010(3.9);3.993(4.2); 3.813(2.0); 3.800(4.4); 3.787(4.0); 3.773(5.7); 3.761 (2.7);3.749(1.1); 3.740(1.3); 3.735(1.3); 3.723(1.7); 3.713(1.6); 3.708(1.6);3.698(1.4); 3.622(2.7); 3.610(3.0); 3.601(3.1); 3.595(2.4); 3.589(3.1);3.583(2.4); 3.574(3.0); 3.567(1.4); 3.562(2.5); 3.559(1.3); 3.549(3.4);3.536(4.0); 3.526(2.6); 3.521 (3.1); 3.515(2.3); 3.512(4.1); 3.504(1.9);3.498(2.0); 3.492(2.0); 3.489(1.7); 3.485(7.5); 3.480(1.9); 3.478(1.6);3.465(1.4); 3.454(1.3); 2.958(15.6); 2.957(16.0); 2.880(13.7);2.878(14.0); 2.288(0.6); 2.279(0.7); 2.273(0.7); 2.264(1.3); 2.253(1.1);2.249 (0.8); 2.244(0.9); 2.239(1.1); 2.229(1.6); 2.220(0.9); 2.214(0.8);2.205(0.7); 2.192(0.7); 2.178(1.2); 2.171(0.7); 2.165(0.9); 2.156(2.9);2.143(3.8); 2.135(2.1); 2.130(2.1); 2.121(3.4); 2.107(4.4); 2.095(3.4);2.083(3.8); 2.071(2.9); 2.060(1.3); 2.048 (1.3); 2.036(0.7); 2.019(0.8);2.008(1.2); 1.998(0.8); 1.991(0.8); 1.984(0.8); 1.980(1.3); 1.974(1.1);1.970(0.9); 1.963(0.6); 1.956(0.6); 1.946(0.9); 1.935(0.6); 1.508(3.9);0.008(0.7); 0.000(24.0); −0.009(0.7) Compound 1542a: 1H-NMR (400.0 MHz.CDCl3): δ = 7.996(2.0); 7.368(1.2); 7.353(1.7); 7.347(4.4); 7.332(5.0);7.327(5.9); 7.313(5.9); 7.307(3.6); 7.292(3.2); 7.266(32.8); 7.259(11.9); 7.087(20.3); 7.078(1.6); 7.076(1.6); 7.072(1.6); 7.070(1.7);7.056(4.1); 7.050(4.7); 7.036(8.0); 7.032(6.2); 7.015 (6.6); 7.010(4.4);6.991(2.4); 6.980(6.2); 6.960(4.9); 6.941(3.4); 6.936(4.3); 6.931(2.6);6.918(3.3); 6.913(4.3); 6.908(2.6); 4.294(8.1); 4.280(8.5); 4.068(4.7);4.052(5.1); 3.853(2.1); 3.840(4.3); 3.826(4.1); 3.813(5.5); 3.800(2.7);3.761(1.2); 3.751 (1.5); 3.747(1.6); 3.734(3.2); 3.724(3.1); 3.719(2.7);3.709(5.0); 3.695(4.8); 3.686(3.2); 3.681(3.8); 3.672(4.3); 3.658(22);3.647 (2.7); 3.636(3.1); 3.625(3.1); 3.620(2.7); 3.614(3.2); 3.609(2.6);3.598(2.4); 3.587(2.2); 3.506(1.5); 3.495(1.7); 3.480(8.0); 3.470(2.1);3.454(1.4); 3.443(1.3); 2.959(16.0); 2.877(13.6); 2.288(0.42.278(0.8);2.273(0.8); 2.264(1.3); 2.253(1.4); 2.249(1.0); 2.239(2.3); 2.228(2.1);2.218(1.8); 2.212(1.6); 2.203(3.3); 2.190(3.3); 2.182(2.1); 2.176(1.9);2.168(2.3); 2.155 (1.5); 2.116(1.6); 2.104(2.4); 2.092(3.0); 2.080(3.2);2.069(2.9); 2.057(1.7); 2.046(1.3); 2.033(0.9); 1.949(0.8); 1.939(1.5);1.992 (0.9); 1.922(0.9); 1.911(1.7); 1.904(1.5); 1.894(0.7); 1.887(0.7);1.876(1.2); 1.866(0.7); 1.729(4.4); 0.008(0.5); 0.000(12.4) Compound1565a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.005(1.3); 7.351(2.1);7.345(2.2); 7.334(2.0); 7.328(2.0); 7.2724(9.5); 7.2715(9.3);7.264(57.7); 7.258(4.0); 7.252(3.7); 7.163(1.3); 7.142(4.7);7.117(17.9); 7.109(2.4); 7.103(2.1); 7.097(5.7); 7.088(0.6); 7.082(0.5);7.060(2.4); 7.054(2.3); 7.050 (2.6); 7.044(2.4); 7.039(1.5); 7.033(1.5);7.028(1.4); 7.022(1.3); 4.269(5.0); 4.255(5.2); 4.046(3.2); 4.029(3.5);3.866(1.4); 3.854(2.9); 3.840(2.7); 3.827(3.7); 3.814(1.8); 3.783(0.8);3.773(1.0); 3.769(1.0); 3.759(1.1); 3.756(1.2); 3.746(1.2); 3.742 (1.2);3.732(1.0); 3.713(0.8); 3.704(0.9); 3.697(0.8); 3.686(1.6); 3.676(2.2);3.669(1.1); 3.661(3.4); 3.658(2.8); 3.653(2.1); 3.647(3.6); 3.638(3.1);3.636(3.0); 3.630(2.0); 3.625(3.6); 3.620(1.9); 3.609(1.7); 3.598(1.5);3.521(1.1); 3.510(1.2); 3.496 (1.5); 3.487(16.0); 3.469(1.0);3.459(0.9); 2.960(11.7); 2.881(9.8); 2.880(9.9); 2.263(0.5); 2.259(0.5);2.249(0.8); 2.238(1.0); 2.232(0.9); 2.228(0.8); 2.224(1.1); 2.219(1.0);2.217(1.0); 2.213(1.2); 2.210(0.9); 2.204(1.3); 2.196(2.0); 2.190(0.8);2.183 (2.0); 2.174(1.4); 2.169(1.3); 2.162(1.3); 2.160(1.4); 2.147(1.0);2.112(1.1); 2.101(1.5); 2.100(1.5); 2.089(2.0); 2.077(2.0); 2.066(1.9);2.054(1.1); 2.043(0.8); 2.041(0.8); 2.030(0.6); 1.939(0.5); 1.929(1.1);1.918(0.6); 1.911(0.6); 1.901(1.2); 1.893 (1.0); 1.866(0.9); 1.564(3.9);0.008(0.7); 0.000(21.5); −0.009(0.6) Compound 1516a: 1H-NMR (400.0 MHz.CDCl3): δ = 7.262(50.0); 7.256(5.1); 7.222(1.7); 7.214(1.9); 7.208(2.1);7.200(1.9); 7.150(2.6); 7.142(3.0); 7.136(3.5); 7.127 (3.2); 7.100(7.5);7.085(0.5); 7.077(0.6); 7.071(2.2); 7.057(3.9); 7.051(3.9); 7.047(1.7);7.043(2.4); 7.037(5.9); 7.022(2.6); 4.259(3.2); 4.250(3.3); 4.038(2.0);4.027(2.1); 3.847(0.9); 3.839(1.9); 3.830(1.8); 3.821(2.2); 3.813(1.0);3.787(0.4); 3.758 (0.6); 3.751(0.7); 3.748(0.7); 3.741(0.9); 3.730(1.3);3.724(1.2); 3.719(0.6); 3.712(1.0); 3.706(0.6); 3.700(0.7); 3.694(1.4);3.685(1.7); 3.678(1.2); 3.669(1.7); 3.660(0.9); 3.634(1.1); 3.627(1.2);3.620(1.3); 3.616(1.2); 3.612(1.3); 3.609(1.1); 3.602 (1.0); 3.595(0.9);3.499(0.6); 3.492(0.9); 3.490(0.8); 3.483(1.0); 3.476(1.0); 3.465(0.6);3.458(0.5); 2.285(0.3); 2.279(0.3); 2.276(0.4); 2.269(0.6); 2.262(0.6);2.253(0.6); 2.246(0.7); 2.239(0.4); 2.236(0.4); 2.230(0.4); 2.227(0.5);2.218(0.7); 2.212 (0.6); 2.209(0.6); 2.203(1.3); 2.195(1.4); 2.189(0.8);2.186(0.7); 2.180(1.0); 2.171(0.6); 2.099(0.6); 2.092(1.0); 2.084(1.2);2.076(1.4); 2.068(1.3); 2.060(0.8); 2.052(0.7); 2.044(0.4); 1.927(0.3);1.920(0.6); 1.913(0.4); 1.908(0.4); 1.901(0.7); 1.896 (0.7); 1.890(0.3);1.885(0.3); 1.878(0.5); 1.541(6.6); 0.005(0.7); 0.000(13.6); −0.006(0.5)Compound 208a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.570(11.1); 8.567(11.4);8.559(11.4); 8.555(11.2); 8.516(6.7); 8.512(6.9); 8.505(6.9);8.501(6.8); 7.718(14.0); 7.715(13.8); 7.698(15.5); 7.694(17);7.535(8.8); 7.531(8.5); 7.522(1.0); 7.515(9.8); 7.511(9.4);7.263(118.6); 7.219(15.9); 7.214(5.0); 7.207(18.3); 7.199(16.3);7.196(6.0); 7.190(6.5); 7.187(19.0); 7.181(8.5); 7.180(8.7); 7.176(4.9);7.169(4.8); 7.164(5.4); 7.160(7.3); 7.155(7.5); 7.135(6.4); 7.110(12.6);7.102(5.9); 7.098(13.8); 7.089(11.1); 7.078(10.7); 7.071(1.9);7.024(2.6); 7.003(4.9); 6.999(3.7); 6.995(3.1); 6.989(3.4); 6.982(4.3);6.977(6.2); 6.970(3.6); 6.968(3.3); 6.962(3.4); 6.958(4.1); 6.949 (2.8);6.944(3.1); 6.906(2.2); 6.903(2.5); 6.901(2.3); 6.896(3.5); 6.893(2.6);6.891(2.3); 6.887(2.3); 6.881(1.9); 6.875(2.3); 6.871(1.7); 6.866(1.3);4.363(8.6); 4.356(12.9); 4.337(11.1); 4.333(16.0); 4.158(2.7);4.141(8.1); 4.131(5.7); 4.123(3.5); 4.117 (9.3); 4.107(8.1); 4.098(2.7);4.094(3.9); 4.083(3.6); 3.625(1.9); 3.611(3.9); 3.597(4.7); 3.583(5.5);3.569(28.); 3.519(2.8); 3.505(5.6); 3.491(6.7); 3.483(11.2); 3.478(9.2);3.464(6.9); 3.455(2.4); 3.449(3.2); 3.437(3.0); 3.421(2.2); 3.408(4.6);3.394 (5.3); 3.388(5.5); 3.380(3.5); 3.374(5.2); 3.367(3.4); 3.360(3.5);3.347(3.1); 2.955(4.5); 2.880(3.8); 2.878(3.7); 2.405(5.2); 2.390(7.5);2.388(7.6); 2.374(6.6); 2.372(7.7); 2.356(4.7); 2.103(2.0); 2.089(4.0);2.079(2.2); 2.075(2.3); 2.068(3.3); 2.065 (4.4); 2.055(5.6); 2.052(2.8);2.045(3.0); 2.041(2.8); 2.031(5.3); 2.017(2.5); 1.883(2.5); 1.872(2.8);1.868(3.0); 1.863(3.0); 1.857(3.0); 1.853(3.3); 1.848(4.5); 1.838(4.5);1.834(2.5); 1.829(2.4); 1.823(2.2); 1.818(2.3); 1.814(2.0); 1.803(1.8);1.624 (2.7); 0.008(1.4); 0.000(44.8); −0.009(1.2) Compound 208a threo:1H-NMR (400.0 MHz. CDCl3): δ = 8.574(1.9); 8.570(2.0); 8.563(2.0);8.559(2.0); 8.519(10.6); 8.515(11.0); 8.508(10.9); 8.504(10.9);7.723(2.4); 7.720(2.4); 7.703(2.6); 7.699(2.5); 7.538(13.3);7.534(13.7); 7.517(15.0); 7.513(14.7); 7.261(206.1); 7.223(2.7);7.217(0.9); 7.211(3.7); 7.202(3.2); 7.199(1.0); 7.191(3.4); 7.182(1.6);7.178(1.0); 7.172(0.9); 7.167(1.1); 7.162(1.4); 7.157(1.5); 7.138(1.2);7.112 (16.2); 7.100(15.5); 7.091(14.3); 7.080(14.1); 7.024(4.2);7.003(7.8); 7.000(5.1); 6.995(4.9); 6.989(5.3); 6.983(6.); 6.978 (9.3);6.971(5.7); 6.968(5.2); 6.962(5.5); 6.958(6.5); 6.950(4.2); 6.944(4.8);6.909(3.6); 6.905(3.9); 6.903(3.7); 6.899(5.6); 6.895(4.2); 6.893(3.7);6.889(3.7); 6.884(2.9); 6.877(3.7); 6.874(2.7); 6.868(2.1); 4.366(12.7);4.360(2.8); 4.341(16.0); 4.160 (4.3); 4.143(7.2); 4.134(4.0);4.126(4.6); 4.117(5.6); 4.109(1.8); 4.100(3.6); 4.085(0.7); 3.631(3.3);3.617(6.8); 3.603(8.4); 3.589(9.6); 3.575(4.9); 3.523(0.6); 3.509(1.1);3.495(1.5); 3.488(5.1); 3.481(2.1); 3.472(7.5); 3.461(3.9); 3.454(5.6);3.443 (5.1); 3.427(3.7); 3.412(1.0); 3.398(1.1); 3.392(1.1); 3.384(0.7);3.378(1.1); 3.371(0.7); 3.364(0.7); 3.351(0.6); 2.409(8.5); 2.393(12.7);2.377(12.6); 2.361(7.8); 2.093(0.7); 2.069(0.8); 2.058(1.5); 2.048(0.5);2.045(0.5); 2.034(0.9); 1.873(0.5); 1.868 (0.6); 1.864(0.6); 1.858(0.6);1.853(0.6); 1.849(0.8); 1.838(0.8); 1.607(3.5); 0.008(2.1); 0.000(77.2);−0.009(2.2) Compound 1531a: 1H-NMR (400.0 MHz. CDCl3): δ = 7.288(3.5);7.262(50.0); 7.188(0.4); 7.174(1.0); 7.168(1.6); 7.155(3.2); 7.139(3.2);7.131(12.3); 7.125(1.8); 7.117 (0.8); 7.112(0.6); 7.109(0.5);7.104(0.5); 7.100(0.4); 7.085(0.3); 7.051(1.5); 7.047(1.6); 7.039(1.7);7.034(2.4); 7.029(1.6); 7.021(1.5); 7.017(1.4); 6.980(0.6); 6.973(0.5);6.966(0.6); 6.922(2.2); 6.915(1.7); 6.907(1.9); 4.268(5.1); 4.260(5.2);4.040 (1.4); 4.029(1.5); 3.857(1.4); 3.849(2.9); 3.840(2.7); 3.831(3.3);3.823(1.6); 3.772(0.4); 3.765(0.6); 3.763(0.5); 3.756(0.6); 3.747(0.7);3.745(0.7); 3.738(0.7); 3.731(0.5); 3.724(0.8); 3.718(0.5); 3.710(1.6);3.701(2.7); 3.694(1.9); 3.692(1.7); 3.685 (2.7); 3.676(1.4); 3.642(1.7);3.635(1.9); 3.628(2.1); 3.624(1.9); 3.621(2.1); 3.618(1.7); 3.610(1.5);3.603(1.4); 3.504(0.5); 3.497(0.6); 3.490(2.3); 3.481(0.8); 3.470(0.4);3.463(0.4); 2.252(0.4); 2.245(0.5); 2.236(0.5); 2.228(0.5); 2.222(0.9);2.214 (1.2); 2.208(0.9); 2.204(0.9); 2.199(1.9); 2.190(2.2); 2.184(1.3);2.181(1.2); 2.175(1.5); 2.166(0.9); 2.107(1.0); 2.100(1.6); 2.092(1.9);2.084(2.0); 2.076(1.9); 2.068(1.3); 2.061(1.0); 2.052(0.6); 1.925(0.5);1.907(0.6); 1.901(0.6); 1.883(0.4); 1.566 (5.3); 0.000(14.6);−0.006(0.5) Compound 1272a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.623(13.3);8.620(13.8); 8.565(11.5); 8.561(11.5); 8.162(16.0); 8.159(15.6);7.926(13.9); 7.922(13.8); 7.519 (6.5); 7.383(2.4); 7.369(2.7);7.364(5.2); 7.349(5.1); 7.344(3.4); 7.329(3.5); 7.310(1.5); 7.308(0.7);7.291(1.3); 7.286(1.7); 7.277(2.8); 7.271(5.2); 7.270(5.8); 7.269(7.2);7.260(1202.0); 7.247(4.0); 7.231(2.5); 7.226(5.9); 7.212(4.5);7.206(3.8); 7.198(1.2); 7.192(2.8); 7.169(1.0); 7.081(8.0); 7.078(6.4);7.075(4.7); 7.060(7.4); 7.058(7.4); 7.054(6.3); 7.052(4.4); 7.043 (4.2);7.038(5.1); 7.033(4.7); 7.020(3.9); 7.016(4.1); 7.010(2.3); 6.996(6.6);6.969(2.1); 6.967(2.1); 6.963(2.2); 6.960(2.4); 6.948(3.4); 6.946(3.8);6.942(3.6); 6.939(4.2); 6.927(1.8); 6.925(1.9); 6.921(1.9); 6.918(2.0);6.888(5.0); 6.886(4.5); 6.881 (3.7); 6.876(4.2); 6.870(6.5); 6.858(3.5);6.852(3.5); 6.847(2.1); 4.302(8.8); 4.280(14.4); 4.254(8.3); 3.725(2.1);3.711(2.6); 3.698(3.0); 3.687(2.9); 3.684(3.0); 3.673(2.5); 3.639(2.2);3.626(4.1); 3.613(6.3); 3.599(5.5); 3.590(5.8); 3.586(5.1); 3.581(5.0);3.566(3.9); 3.556(3.7); 3.348(2.6); 3.337(4.0); 3.326(4.5); 3.321(2.9);3.314(5.9); 3.310(4.4); 3.303(3.3); 3.299(4.3); 3.287 (4.6); 3.276(2.4);2.502(1.0); 2.493(1.2); 2.488(1.4); 2.479(2.1); 2.467(1.8); 2.453(1.9);2.444(2.7); 2.435(1.6); 2.429(1.4); 2.421(1.3); 2.276(1.5); 2.265(3.0);2.254(1.4); 2.249(1.5); 2.238(3.0); 2.230(2.5); 2.220(1.2); 2.214(1.2);2.203(2.1); 2.192 (1.0); 2.089(1.0); 2.078(2.0); 2.065(1.6); 2.053(2.7);2.043(4.0); 2.030(2.7); 2.017(3.6); 2.006(2.1); 1.977(1.8); 1.964(2.6);1.954(2.2); 1.952(2.4); 1.942(3.3); 1.929(3.0); 1.919(1.2); 1.908(1.3);1.894(0.9); 1.529(6.9); 1.255(1.0); 0.331(1.0); 0.238 (0.8); 0.157(1.8);0.146(1.2); 0.008(12.9); 0.000(468.1); −0.009(13.6); −0.150(1.4)Compound 1700a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.005(1.8); 7.291(3.2);7.285(3.4); 7.274(3.2); 7.269(3.7); 7.262(60.2); 7.230(6.1); 7.224(6.4);7.213(6.3); 7.207(6.3); 7.123 (1.7); 7.116(5.3); 7.102(6.4);7.094(14.3); 7.086(3.5); 7.081(7.6); 7.073(11.9); 7.069(3.7);7.065(1.2); 7.059(1.0); 7.053 (0.8); 7.044(4.5); 7.038(4.3); 7.032(4.8);7.027(4.4); 7.022(2.8); 7.016(2.5); 7.011(2.4); 7.005(2.2); 6.998(0.5);6.378(3.1); 6.377(3.1); 6.373(5.8); 6.372(5.8); 6.369(6.4); 6.364(10.8);6.355(6.5); 6.282(10.0); 6.278(10.1); 6.272(8.2); 6.268(8.1); 6.261(5.1); 6.256(5.1); 6.251(4.3); 6.247(4.2); 4.138(9.2); 4.124(9.5);3.950(5.1); 3.931(5.5); 3.819(2.4); 3.806(5.3); 3.792(5.1); 3.779(7.2);3.770(1.8); 3.766(3.6); 3.761(1.7); 3.756(1.6); 3.744(2.1); 3.734(1.9);3.729(1.9); 3.719(1.7); 3.653(3.3); 3.641 (3.7); 3.632(3.8); 3.626(2.9);3.620(3.8); 3.614(2.9); 3.605(2.8); 3.593(2.6); 3.562(1.7); 3.550(1.9);3.538(2.1); 3.535(1.7); 3.526(2.1); 3.523(1.8); 3.511(1.6); 3.499(1.4);3.485(6.8); 3.458(0.7); 3.450(1.0); 3.441(1.0); 3.433(2.1); 3.429(2.2);3.420 (3.2); 3.413(3.5); 3.404(3.2); 3.396(3.3); 3.390(2.6); 3.381(1.3);3.375(1.2); 2.958(16.0); 2.880(13.4); 2.879(12.9); 2.281(0.7);2.272(0.7); 2.267(0.8); 2.258(1.5); 2.247(1.2); 2.243(0.9); 2.237(1.0);2.232(1.2); 2.223(1.8); 2.214(0.9); 2.208(0.9); 2.199 (0.8); 2.146(0.8);42.133(1.7); 2.125(0.9); 2.120(1.1); 2.111(3.5); 2.098(4.8); 2.090(2.8);2.085(2.4); 2.077(4.2); 2.071(2.5); 2.063(2.5); 2.059(4.6); 2.047(4.3);2.035(4.6); 2.023(3.4); 2.012(1.7); 2.000(1.7); 1.988(0.8); 1.952(0.9);1.941(1.4); 1.930 (0.9); 1.923(0.9); 1.917(1.); 1.913(1.5); 1.906(1.3);1.902(1.0); 1.896(0.8); 1.888(0.8); 1.878(1.1); 1.867(0.7); 1.489(10.1);0.008(0.7); 0.000(22.5); −0.009(0.7) Compound 1538a: 1H-NMR (400.0 MHz.CDCl3): δ = 7.345(0.7); 7.341(0.7); 7.334(0.7); 7.330(0.7); 7.300(2.5);7.262(50.0); 7.253(2.3); 7.250(2.1); 7.154(0.6); 7.142 (8.3);7.130(2.0); 7.126(1.2); 7.116(4.3); 7.107(0.7); 7.102(2.8); 7.093(0.3);7.085(0.4); 7.045(1.3); 7.041(1.4); 7.038(1.5); 7.034(1.4); 7.032(1.1);7.027(1.0); 7.024(1.0); 7.020(0.8); 4.258(3.3); 4.249(3.4); 4.039(1.1);4.028(1.1); 3.858(0.9); 3.850 (1.9); 3.841(1.8); 3.832(2.2); 3.824(1.1);3.773(0.3); 3.766(0.4); 3.764(0.4); 3.755(0.5); 3.748(0.4); 3.746(0.5);3.740(0.5); 3.735(0.4); 3.730(0.3); 3.723(0.6); 3.716(0.4); 3.711(0.4);3.706(1.2); 3.697(1.8); 3.690(1.2); 3.687(1.1); 3.681(1.8); 3.672 (0.9);3.644(1.1); 3.638(1.2); 3.630(1.3); 3.627(1.2); 3.623(1.3); 3.620(1.2);3.612(1.0); 3.605(0.9); 3.505(0.4); 3.498(0.4); 3.491(2.3); 3.481(0.5);3.471(0.3); 2.243(0.3); 2.236(0.4); 2.227(0.4); 2.220(0.7); 2.211(0.9);2.206(0.6); 2.203(0.7); 2.197 (1.3); 2.188(1.4); 2.182(0.8); 2.179(0.8);2.173(1.0); 2.164(0.6); 2.103(0.6); 2.095(1.0); 2.088(1.2); 2.080(1.4);2.072(1.3); 2.064(0.8); 2.056(0.6); 2.049(0.4); 1.925(0.3); 1.906(0.4);1.901(0.4); 1.556(3.1); 0.005(0.7); 0.000(14.1); −0.006(0.5) Compound532a erythro: 1H-NMR (400.0 MHz. CDCl3): δ = 8.341(1.2); 8.321(12.7);8.320(12.5); 8.309(12.9); 8.307(12.9); 7.519(43); 7.360(0.9);7.309(0.9); 7.292(1.8); 7.286(1.4); 7.283(1.6); 7.271(3.9); 7.269(5.3);7.260(812.3); 7.210(2.6); 7.163(0.5); 7.156(4.4); 7.135(7.0);7.132(5.1); 7.115(6.6); 7.111 (7.8); 7.097(1.1); 7.090(4.7);7.036(13.8); 7.033(14.0); 7.032(16.0); 7.019(4.5); 7.013(4.3);7.001(4.1); 6.996(8.9); 6.992 (14.5); 6.988(11.4); 6.979(10.3);6.975(11.6); 6.969(4.0); 6.866(2.4); 6.861(3.4); 6.856(4.5); 6.852(3.3);6.845(3.5); 6.840 (2.9); 6.834(3.8); 6.830(2.7); 6.825(1.9);5.299(12.0); 4.260(11.2); 4.244(11.5); 4.032(1.0); 4.014(1.0);3.783(2.3); 3.770(2.5); 3.757(2.8); 3.748(2.8); 3.735(1.3); 3.531(1.3);3.520(2.3); 3.509(2.5); 3.498(2.9); 3.472(1.9); 3.461(1.1); 3.351(3.1);3.336 (5.6); 3.328(3.8); 3.320(3.4); 3.313(5.7); 3.297(2.9); 2.194(1.1);2.180(1.7); 2.173(1.4); 2.167(1.5); 2.159(4.4); 2.146(5.1); 2.137(3.7);2.135(2.9); 2.131(3.1); 2.123(3.9); 2.115(3.0); 2.110(3.0); 2.103(4.9);2.092(4.3); 2.080(5.2); 2.068(4.3); 2.056 (1.7); 2.044(3.6); 2.032(1.2);1.541(142.4); 1.491(0.8); 1.440(1.0); 1.425(1.0); 1.362(5.0);1.333(2.7); 1.284(3.9); 1.256(5.8); 0.880(1.2); 0.146(1.0); 0.032(0.8);0.008(9.6); 0.000(325.0); −0.009(9.2); −0.050(1.0); −0.150(0.9) Compound647a: 1H-NMR (600.1 MHz. CDCl3): δ = 8.185(0.3); 8.181(0.3); 8.041(0.3);8.031(0.4); 8.027(0.4); 8.018(0.3); 7.449(0.3); 7.446(0.3); 7.438(0.3);7.433 (0.4); 7.261(50.0); 7.211(0.4); 7.197(0.7); 7.058(0.3);7.054(0.3); 7.051(0.3); 7.047(0.5); 7.037(0.4); 7.032(0.4); 7.025(0.7);7.011(0.8); 6.842(0.4); 6.833(0.4); 6.828(0.4); 6.819(0.3); 4.211(0.4);4.194(0.4); 4.144(0.7); 4.126(0.7); 3.758(0.4); 3.749 (0.4); 3.740(0.4);1.557(3.5); 0.000(13.9); −0.006(0.5) Compound 1137a: 1H-NMR (600.1 MHz.CDCl3): δ = 8.095(3.2); 8.086(8.3); 8.076(5.9); 7.303(1.9); 7.290(4.4);7.279(4.1); 7.277(4.2); 7.263(42.9); 7.024(1.7); 7.021 (1.8);7.010(4.0); 7.007(3.4); 6.996(3.2); 6.983(3.0); 6.970(2.1); 6.952(2.0);6.946(4.5); 6.933(4.6); 6.900(3.2); 6.884 (3.2); 6.700(2.4); 6.691(2.4);6.671(4.7); 6.663(4.6); 6.528(4.4); 6.487(8.6); 4.193(5.8); 4.181(5.9);4.027(0.4); 4.012(3.0); 4.000 (3.0); 3.908(50.0); 3.708(1.5);3.699(3.0); 3.690(3.2); 3.681(3.4); 3.672(1.7); 3.645(0.8); 3.638(1.0);3.635(1.0); 3.628(1.6); 3.620(1.1); 3.617(1.0); 3.610(0.9); 3.488(3.6);3.485(2.0); 3.476(2.0); 3.471(2.0); 3.467(1.8); 3.462(2.1); 3.458(1.8);3.453 (1.6); 3.445(1.5); 3.378(0.9); 3.370(1.0); 3.362(1.3); 3.354(1.2);3.345(0.9); 3.337(0.8); 3.298(1.9); 3.288(3.2); 3.282(3.3); 3.277(2.4);3.272(2.9); 3.262(1.9); 2.265(0.4); 2.259(0.5); 2.255(0.5); 2.249(0.8);2.242(0.9); 2.232(0.9); 2.226(1.0); 2.220 (0.6); 2.216(0.6); 2.210(0.5);2.107(0.8); 2.097(1.5); 2.095(1.4); 2.083(2.9); 2.074(4.4); 2.066(4.7);2.060(6.6); 2.050(6.6); 2.043(6.4); 2.034(4.8); 2.027(2.9); 2.019(2.3);2.011(1.4); 0.000(11.5) Compound 1558a: 1H-NMR (400.0 MHz. CDCl3): δ =7.997(2.2); 7.266(38.5); 7.258(12.2); 7.199(1.5); 7.179(3.9);7.159(6.1); 7.136(6.6); 7.125(2.3); 7.115(4.9); 7.105(20.5); 7.093(1.9); 7.067(2.6); 7.061(2.8); 7.049(2.8); 7.042(3.8); 7.035(3.0);7.022(2.6); 7.017(2.7); 6.997(1.3); 6.992(1.7); 6.987(2.2); 6.983(1.9);6.977(1.8); 6.971(1.5); 6.966(1.8); 6.961(1.5); 6.939(2.9); 6.934(3.6);6.929(3.0); 6.923(2.8); 6.918(2.6); 6.913(3.0); 6.908(2.4); 4.283(7.9);4.269(8.2); 4.050(4.7); 4.033(5.2); 3.861(2.1); 3.849(4.3); 3.835(4.2);3.822(5.4); 3.809(2.7); 3.779(1.3); 3.769(1.6); 3.765(1.7); 3.752(2.0);3.742(2.0); 3.738(2.0); 3.728(1.6); 3.716(1.4); 3.707(1.6); 3.699(1.4);3.689 (2.8); 3.680(3.7); 3.666(4.8); 3.657(3.6); 3.652(5.4); 3.642(5.9);3.630(5.3); 3.625(3.3); 3.619(3.5); 3.614(2.8); 3.603(2.4); 3.592(2.2);3.517(1.5); 3.506(1.8); 3.491(2.6); 3.483(7.9); 3.466(1.5); 3.455(1.4);2.961(16.0); 2.878(13.9); 2.280(0.7); 2.270 (0.8); 2.266(0.9);2.256(1.3); 2.245(1.6); 2.232(2.5); 2.220(2.5); 2.210(2.1); 2.205(1.9);2.196(3.5); 2.183(3.2); 2.174(2.2); 2.169(2.1); 2.160(2.4); 2.148(1.5);2.113(1.7); 2.101(2.5); 2.090(3.1); 2.078(3.3); 2.067(2.9); 2.055(1.7);2.043(1.4); 2.031 (0.9); 1.937(0.9); 1.927(1.6); 1.917(1.0); 1.910(0.9);1.900(1.9); 1.892(1.); 1.882(0.8); 1.875(0.8); 1.864(1.4); 1.854(0.7)1.706(4.1); 0.008(0.7); 0.000(14.6); −0.008(0.6) Compound 1295a: 1H-NMR(400.0 MHz. CDCl3): δ = 8.623(14.4); 8.620(15.2); 8.570(12.8);8.566(13.8); 8.199(15.6); 8.196(16.0); 7.971(13.3); 7.968(14.3); 7.519(4.0); 7.385(7.9); 7.367(6.7); 7.260(668.8); 7.237(14.3); 7.231(13.7);7.220(11.5); 7.214(10.7); 7.171(18.4); 7.168(19.9); 7.157(11.6);7.153(17.4); 7.038(5.1); 7.017(11.7); 6.996(12.9); 6.981(5.7);6.976(6.1); 6.970(6.5); 6.965(6.1); 4.281(15.1); 4.260(12.8);4.256(11.9); 3.733(2.4); 3.721(4.4); 3.706(4.1); 3.693(4.5); 3.681(3.3);3.645(3.3); 3.632(5.5); 3.619(5.8); 3.605 (8.3); 3.593(7.4); 3.579(7.2);3.569(8.6); 3.556(6.1); 3.545(5.8); 3.533(3.5); 3.346(3.1); 3.335(4.2);3.320(6.5); 3.307(6.8); 3.297(6.7); 3.285(4.0); 3.280(3.4); 3.269(2.7);2.464(2.3); 2.452(2.9); 2.442(2.9); 2.430(2.8); 2.420(2.0); 2.229(3.2);2.202 (3.7); 2.194(3.2); 2.167(2.6); 2.058(1.4); 2.047(2.2); 2.035(2.1);2.023(3.6); 2.012(4.8); 1.999(3.6); 1.987(4.2); 1.952(2.1); 1.940(3.6);1.930(3.5); 1.918(4.4); 1.905(3.8); 1.883(2.0); 1.509(8.9); 0.146(1.3);0.000(252.0); −0.150(1.8) Compound 289a erythro: 1H-NMR (400.0 MHz.CDCl3): δ = 8.401(3.2); 8.395(3.4); 7.975(2.5); 7.380(0.9); 7.375(1.1);7.369(0.8); 7.358(1.0); 7.352(1.2); 7.347(0.8); 7.269(0.5); 7.268 (0.6);7.267(0.7); 7.261(42.5); 7.170(0.8); 7.149(1.4); 7.146(0.9); 7.129(1.1);7.125(1.3); 7.104(0.8); 7.037(0.7); 7.031(0.7); 7.019(0.7); 7.012(0.9);7.005(0.7); 6.993(0.6); 6.987(0.7); 6.890(0.5); 6.887(0.7); 6.881(0.9);6.877(0.7); 6.871(0.6); 6.865 (0.6); 6.860(0.7); 6.856(0.5);5.299(16.0); 4.487(2.1); 4.472(2.1); 3.633(0.9); 3.616(0.9); 3.092(0.9);3.072(0.9); 3.049(1.4); 3.029(1.3); 2.907(1.4); 2.891(1.4); 2.864(1.0);2.848(0.9); 0.000(15.4) Compound 107a: 1H-NMR (400.0 MHz. CDCl3): δ =8.492(0.7); 8.489(1.4); 8.485(0.8); 8.481(0.8); 8.477(1.4); 8.474(0.8);8.419(0.7); 8.416(1.3); 8.412(0.8); 8.408(0.8); 8.405 (1.38.401(0.7);7.434(0.8); 7.430(0.8); 7.416(1.4); 7.413(1.4); 7.410(2.6); 7.407(1.1);7.399(1.3); 7.393(1.4); 7.390(1.2); 7.386(1.1); 7.295(1.3); 7.2843(1.6);7.2835(1.5); 7.273(1.7); 7.271(0.5); 7.270(0.5); 7.269(0.5); 7.268(0.6);7.2674(0.7); 7.2666 (0.8); 7.266(1.0); 7.261(77.3); 7.2543(1.0);7.2536(1.0); 7.252(1.2); 7.248(0.6); 7.243(0.8); 7.241(0.8); 7.237(1.2);7.233 (1.0); 7.227(0.9); 7.221(1.1); 7.220(1.5); 7.216(2.1); 7.197(1.3);7.193(1.2); 7.177(1.4); 7.172(2.5); 7.166(3.3); 7.155(2.4); 7.151(3.2);7.145(1.2); 7.134(0.7); 7.130(1.2); 7.009(1.0); 7.004(1.0); 6.997(1.2);6.992(1.0); 6.986(1.8); 6.965(2.4); 6.944 (0.8); 4.345(1.8); 4.337(1.7);4.321(2.0); 4.311(1.9); 4.148(1.1); 4.130(3.3); 4.112(3.4); 4.094(1.1);3.906(0.7); 3.896(0.6); 3.892(0.8); 3.889(0.6); 3.881(0.8); 3.661(0.8);3.648(1.0); 3.634(1.0); 3.620(0.6); 3.535(0.7); 3.522(1.0); 3.508(1.1);3.500(0.6); 3.494(0.7); 3.486(0.5); 3.480(0.6); 3.466(0.7); 3.410(0.6);3.397(0.7); 3.390(0.7); 3.377(0.7); 2.410(0.9); 2.406(0.6); 2.401 (0.6);2.396(1.0); 2.387(0.9); 2.374(0.9); 2.043(16.0); 2.036(0.5); 2.024(0.5);1.841(0.5); 1.830(0.5); 1.625(0.8); 1.286(0.7); 1.284(0.7); 1.276(4.9);1.258(10.4); 1.241(4.8); 0.008(0.8); 0.000(27.6); −0.009(0.8) Compound597a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.373(13.1); 8.185(16.0);7.421(0.7); 7.419(0.7); 7.406(1.0); 7.402(1.7); 7.400(1.4); 7.388(1.5);7.384(1.6); 7.381(1.2); 7.370 (0.7); 7.366(1.0); 7.293(0.6);7.261(45.8); 7.239(1.0); 7.224(1.7); 7.219(1.4); 7.215(1.6); 7.211(0.9);7.205(1.47.202(1.7); 7.198(1.6); 7.194(1.0); 7.183(1.7); 7.174(1.8);7.171(2.9); 7.168(2.0); 7.151(2.1); 7.117(3.6); 7.114(3.5); 7.095(4.4);7.092 (4.2); 7.076(1.2); 7.074(1.2); 7.070(0.7); 6.997(0.5); 6.969(3.1);6.954(4.2); 6.949(5.1); 6.941(2.5); 6.936(3.2); 6.933(3.4); 6.928(2.4);6.923(1.5); 6.920(1.7); 6.914(0.7); 5.298(2.5); 4.274(3.2); 4.249(3.7);4.205(3.6); 4.178(4.6); 3.996(1.0); 3.987 (1.0); 3.968(1.7); 3.959(1.7);3.941(0.8); 3.931(0.8); 3.909(0.8); 3.897(0.8); 3.883(1.3); 3.871(1.3);3.857(0.7); 3.845(0.7); 3.768(1.1); 3.755(1.8); 3.741(2.2); 3.728(2.0);3.715(1.3); 3.607(0.9); 3.594(1.5); 3.581(2.0); 3.567(1.8); 3.554(1.1);3.480 (1.2); 3.468(1.4); 3.457(1.5); 3.453(1.3); 3.446(1.5); 3.441(1.3);3.430(1.2); 3.419(1.1); 3.395(1.0); 3.383(1.1); 3.372(1.2); 3.368(1.0);3.360(1.2); 3.356(1.0); 3.346(0.9); 3.334(0.8); 2.955(2.8); 2.879(2.4);2.564(0.6); 2.554(0.7); 2.550(0.7); 2.541 (1.0); 2.529(1.2); 2.518(1.2);2.506(1.3); 2.497(0.8); 2.493(0.7); 2.483(0.7); 2.317(0.5); 2.306(1.0);2.293(0.7); 2.290(0.7); 2.286(0.6); 2.278(1.1); 2.274(1.0); 2.271(1.0);2.267(0.8); 2.259(0.6); 2.255(0.5); 2.243(0.7); 2.073(0.6); 2.061(0.5);2.050 (0.8); 2.047(0.8); 2.042(0.7); 2.038(1.0); 2.035(0.8); 2.024(0.7);2.012(0.8); 1.932(0.6); 1.919(0.9); 1.906(0.8); 1.897(1.2); 1.884(1.1);1.874(0.5); 1.862(0.6); 1.516(1.5); 0.008(0.8); 0.000(18.0); −0.009(0.7)Compound 599a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.379(14.7); 8.197(16.0);7.519(0.8); 7.392(0.8); 7.387(1.2); 7.375(14.4); 7.370(10.1);7.358(5.7); 7.352(1.3); 7.341(1.0); 7.336(1.7); 7.295(0.5); 7.280(2.3);7.275(3.5); 7.270(2.3); 7.269(2.3); 7.267(1.9); 7.260(141.7);7.254(2.3); 7.236(1.1); 7.233 (1.6); 7.231(1.9); 7.228(2.2); 7.212(9.1);7.209(9.1); 7.193(3.1); 7.190(2.0); 7.174(4.3); 7.172(3.5); 7.156(1.7);7.153(1.8) 7.075(1.9); 7.071(2.9); 7.056(1.4); 7.053(2.37); 6.996(0.9);4.249(3.8); 4.224(4.4); 4.180(3.9); 4.152(5.1); 3.989(0.9); 3.979;(0.9); 3.961(1.6); 3.952(1.5); 3.934(0.8); 3.924(0.7); 3.898(0.8);3.886(0.43.872(1.4); 3.860(1.4); 3.845(0.43.834(0.7); 3.773(1.0);3.760(1.6); 3.746(2.0); 3.733(1.9); 3.720(1.2); 3.610(0.9); 3.597(1.5);3.583(2.1); 3.570(1.8); 3.557(1.2); 3.481 (1.1); 3.470(1.2); 3.458(1.3);3.454(1.2); 3.447(1.3); 3.442(1.2); 3.431(1.1); 3.420(1.0); 3.396(1.1);3.384(1.1); 3.374(1.2); 3.369(1.0); 3.362(1.2); 3.357(1.0); 3.347(0.9);3.335(0.9); 2.560(0.5); 2.550(0.6); 2.546(0.6); 2.537(1.0); 2.525(1.1);2.514(1.1); 2.502(1.3); 2.492(0.8); 2.489(0.8); 2.479(0.7); 2.308(0.9);2.296(0.6); 2.292(0.7); 2.284(0.8); 2.280(1.0); 2.277(0.9); 2.273 (0.9);2.269(0.8); 2.261(0.5); 2.257(0.5); 2.245(0.7); 2.068(0.6); 2.045(0.8);2.041(0.9); 2.037(0.8); 2.033(1.1); 2.029(0.9); 2.018(0.7); 2.006(0.9);1.922(0.7); 1.908(0.9); 1.896(0.8); 1.887(1.3); 1.873(1.2); 1.864(0.6);1.852(0.6); 0.008(1.6); 0.000 (53.0); −0.009(1.6) Compound 100a: 1H-NMR(400.0 MHz. CDCl3): δ = 8.503(1.6); 8.500(2.5); 8.497(1.6); 8.491(1.7);8.488(2.5); 8.418(2.2); 8.414(1.4); 8.409(1.4); 8.406(2.2); 7.519(0.9);7.469 (1.1); 7.465(1.2); 7.447(1.8); 7.445(2.4); 7.424(1.5); 7.421(1.5);7.325(1.6); 7.313(2.5); 7.303(2.3); 7.292(1.9); 7.282(1.7);7.260(161.3); 7.242(2.3); 7.239(2.3); 7.224(1.4); 7.219(2.8);7.216(3.0); 7.206(1.4); 7.198(3.4); 7.191(2.6); 7.187(3.3); 7.176 (3.5);7.166(1.9); 7.155(0.9); 7.150(1.5); 7.115(1.1); 7.110(1.4);7.095(0.47.089(0.9); 7.025(0.9); 7.004(1.47.001(1.2); 6.996(1.1);6.984(1.5); 6.980(2.5); 6.974(1.1); 6.959(1.6); 6.956(1.3); 6.947(1.1);6.934(0.9); 6.929(1.0); 6.881(0.9); 6.876 (1.2); 6.871(1.0); 6.865(0.9);6.854(0.9); 4.351(3.0); 4.337(2.6); 4.326(3.3); 4.311(2.9); 4.150(1.2);4.132(3.5); 4.115(3.5); 4.097(1.2); 3.950(0.6); 3.939(0.6); 3.928(1.4);3.918(1.4); 3.904(1.6); 3.893(1.5); 3.880(0.7); 3.871(0.6); 3.696(0.7);3.682(1.3); 3.668(1.5); 3.654(1.8); 3.641(1.0); 3.557(0.8); 3.543(1.5);3.529(2.1); 3.515(2.7); 3.501(1.7); 3.491(0.7); 3.485(0.8); 3.472 (0.7);3.423(1.1); 3.410(1.2); 3.402(1.3); 3.395(0.9); 3.389(1.2); 3.382(0.9);3.375(0.9); 3.362(0.8); 2.427(0.8); 2.417(1.5); 2.403(1.9); 2.394(1.8);2.381(1.9); 2.368(0.8); 2.233(7.8); 2.107(1.2); 2.091(0.8); 2.079(0.8);2.067(1.0); 2.056(1.3); 2.046 (16.0); 2.032(1.1); 2.019(0.5);1.882(0.6); 1.867(0.7); 1.862(0.7); 1.857(0.7); 1.847(1.0); 1.837(1.0);1.827(0.6); 1.277(4.2); 1.260(8.4); 1.242(4.1); 0.069(5.8); 0.008(2.6);0.000(57.3); −0.009(2.1) Compound 620a: 1H-NMR (400.0 MHz. CDCl3): δ =8.381(16.0); 8.369(1.1); 8.243(1.1); 8.214(15.4); 7.519(5.4);7.293(0.6); 7.289(0.8); 7.260(956.7); 7.250(5.0); 7.244(2.3);7.229(3.0); 7.226(3.7); 7.218(2.0); 7.209(3.2); 7.205(3.4); 7.200(1.8);7.185(2.0); 7.147(0.6); 7.128(1.3); 7.122 (1.8); 7.118(1.4); 7.112(1.2);7.101(1.3); 7.093(1.8); 7.087(1.4); 7.071(2.0); 7.061(1.4); 7.050(3.1);7.043(1.5); 7.030(1.9); 7.026(2.2); 7.006(1.7); 6.996(5.4); 6.921(1.6);5.299(2.1); 4.265(3.9); 4.240(4.4); 4.184(3.4); 4.157(4.4); 3.974(0.8);3.965(0.8); 3.946(1.4); 3.936(1.4); 3.917(0.7); 3.908(0.6); 3.887(0.8);3.875(0.8); 3.861(1.4); 3.848(1.4); 3.836(0.9); 3.823(0.7); 3.779(0.9);3.766(1.4); 3.753(1.8); 3.740(1.7); 3.726(1.1); 3.636(1.0); 3.623(1.6);3.610(2.0); 3.597(1.9); 3.583(1.2); 3.478(0.9); 3.467(1.1); 3.456(1.1);3.444(1.2); 3.428(1.0); 3.411(1.0); 3.399(1.1); 3.388(1.2); 3.377(1.2);3.362(0.9); 3.350(0.9); 2.544 (0.6); 2.535(0.9); 2.522(1.0); 2.510(1.0);2.499(1.3); 2.490(0.7); 2.476(0.6); 2.294(0.8); 2.266(0.9); 2.231(0.7);2.040(1.1); 2.013(0.9); 2.005(0.7); 1.936(0.7); 1.923(1.); 1.912(0.9);1.901(1.4); 1.888(1.2); 1.878(0.7); 1.865(0.7); 1.543(11.9); 1.371(0.9); 1.333(1.7); 1.284(2.4); 1.256(2.2); 0.146(1.0); 0.008(9.1);0.000(336.9); −0.009(9.9); −0.150(1.0) Compound 84a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.385(4.0); 8.377(5.5); 8.374(7.4); 8.368(6.9); 8.201(3.7);7.959(6.9); 7.351(2.4); 7.345(3.2); 7.340(2.5); 7.328(3.5); 7.322 (3.5);7.316(2.8); 7.307(3.5); 7.291(4.2); 7.286(4.9); 7.278(2.6); 7.272(6.6);7.262(66.2); 7.251(4.4); 7.244(1.5); 7.041(1.1); 7.034(1.4); 7.029(1.9);7.022(3.0); 7.013(2.3); 7.010(3.1); 7.008(3.1); 7.003(3.4); 7.001(3.5);6.995(1.3); 6.989(1.6); 6.987 (1.6); 6.982(1.7); 6.966(2.4); 6.956(1.5);6.950(3.1); 6.947(3.6); 6.932(1.6); 6.927(1.8); 6.922(1.0); 6.887(4.0);6.868(3.8); 6.858(2.8); 6.853(3.1); 6.848(1.8); 6.835(2.4); 6.830(3.0);6.825(1.8); 5.299(16.0); 4.307(5.9); 4.292(6.1); 4.057(3.2); 4.040(3.4); 3.835(1.2); 3.798(1.6); 3.785(3.4); 3.772(3.5); 3.758(4.1);3.745(2.43.690(0.9); 3.679(1.1); 3.675(1.1); 3.664(1.6); 3.653(1.3);3.648(1.2); 3.638(1.0); 3.547(1.9); 3.535(2.2); 3.526(2.3); 3.520(2.0);3.514(2.4); 3.509(2.1); 3.499(2.4); 3.487 (2.3); 3.474(2.4); 3.460(2.7);3.446(2.0); 3.437(2.3); 3.422(1.1); 3.385(1.0); 3.373(1.2); 3.361(1.4);3.349(1.4); 3.346(1.2); 3.335(1.0); 3.323(0.9); 2.320(0.5); 2.315(0.5);2.305(0.9); 2.295(1.0); 2.284(0.9); 2.280(1.0); 2.270(1.2); 2.259(1.1);2.245(1.5); 2.237(0.8); 2.231(0.9); 2.223(2.2); 2.209(2.6); 2.202(1.6);2.195(1.5); 2.188(2.0); 2.174(1.3); 2.170(1.1); 2.162(1.3); 2.150 (2.3);2.138(2.2); 2.127(2.8); 2.114(2.5); 2.102(1.8); 2.091(1.6); 2.084(0.8);2.078(1.0); 2.073(1.2); 2.065(1.0); 2.054(0.6); 2.048(0.6); 2.043(0.8);2.038(0.8); 2.005(0.9); 1.752(1.5); 1.371(0.6); 1.286(0.9); 1.258(1.4);0.008(1.0); 0.000(25.2); −0.009(1.2) Compound 295a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.492(0.8); 8.488(1.6); 8.485(0.9); 8.480(0.9); 8.477(1.6);8.473(0.9); 8.421(0.8); 8.417(1.5); 8.414(0.9); 8.410(0.8); 8.406 (1.5);8.403(0.8); 7.557(1.4); 7.551(1.5); 7.541(1.4); 7.535(1.5); 7.431(0.9);7.428(0.9); 7.410(1.3); 7.407(1.5); 7.404(1.0); 7.387(1.2); 7.383(1.1);7.308(1.4); 7.302(1.5); 7.299(0.9); 7.293(3.2); 7.287(1.8); 7.282(2.5);7.278(1.2); 7.272(2.5); 7.266 (1.7); 7.261(74.3); 7.250(1.0);7.239(0.7); 7.236(0.8); 7.218(1.4); 7.216(0.9); 7.215(1.4); 7.213(0.9);7.195(1.4); 7.192(1.3); 7.177(1.4); 7.166(2.4); 7.155(1.6); 7.148(2.0);7.145(1.3); 7.134(0.7); 7.127(2.8); 7.107(1.5); 7.079(0.6); 7.073(0.6);7.067 (0.7); 7.062(0.6); 7.057(0.9); 7.051(0.9); 7.046(0.9); 7.040(0.8);6.965(1.9); 6.944(2.7); 6.923(1.3); 4.342(2.0); 4.332(1.8); 4.318(2.2);4.306(2.0); 4.148(1.1); 4.130(3.3); 4.112(3.3); 4.094(1.1); 3.903(0.9);3.892(0.7); 3.889(0.9); 3.878(0.9); 3.662(0.9); 3.648(1.0); 3.634(1.0);3.621(07); 43.535(0.8); 3.522(1.1); 3.508(1.2); 3.501(0.7); 3.494(0.7);3.486(0.6); 3.481(0.7); 3.467 (0.7); 3.453(0.5); 3.411(0.6); 3.398(0.7);3.390(0.7); 3.383(0.5); 3.377(0.7); 2.419(0.5); 2.409(0.8); 2.405(0.6);2.396(1.0); 2.387(1.1); 2.374(1.2); 2.095(0.9); 2.057(0.5); 2.043(16.0);2.035(0.6); 2.023(0.6); 1.842(0.6); 1.831(0.6); 1.588(0.7); 1.333 (0.7);1.284(1.1); 1.276(4.9); 1.258(10.4); 1.240(4.8); 0.008(0.8);0.000(27.5); −0.009(0.7) Compound 619a: 1H-NMR (400.0 MHz. CDCl3): δ =8.384(14.1); 8.219(16.0); 7.588(2.5); 7.582(2.7); 7.572(2.6);7.566(2.7); 7.519(1.1); 7.431(2.4); 7.425(2.6); 7.415(2.5); 7.410 (2.6);7.325(1.3); 7.319(1.3); 7.314(1.5); 7.308(1.4); 7.304(1.9); 7.298(1.9);7.293(2.0); 7.287(1.7); 7.260(176.1); 7.191 (3.4); 7.170(4.9);7.150(2.8); 7.122(1.3); 7.116(1.2); 7.111(1.3); 7.105(1.3); 7.101(1.7);7.095(1.7); 7.089(1.7); 7.084(1.6); 7.010(3.9); 6.996(1.3); 6.990(5.2);6.969(2.6); 4.258(3.5); 4.233(4.0); 4.176(3.8); 4.148(4.9); 3.972(0.9);3.962(0.9); 3.944 (1.5); 3.935(1.5); 3.917(0.7); 3.907(0.7); 3.879(0.8);3.867(0.8); 3.853(1.4); 3.841(1.4); 3.828(0.8); 3.816(0.7); 3.780(1.1);3.767(1.7); 3.753(2.0); 3.740(2.0); 3.727(1.3); 3.632(1.0); 3.619(1.6);3.606(2.1); 3.593(2.0); 3.580(1.3); 3.477(1.2); 3.466(1.3); 3.454(1.4);3.450(1.3); 3.443(1.4); 3.439(1.3); 3.427(1.2); 3.415(1.1); 3.409(1.2);3.397(1.2); 3.386(1.3); 3.382(1.1); 3.375 (1.3); 3.371(1.1); 3.360(1.0);3.348(1.0); 2.553(0.6); 2.543(0.6); 2.539(0.6); 2.530(1.0); 2.518(1.1);2.507(1.1); 2.495(1.2); 2.485(0.8); 2.482(0.8); 2.472(0.6); 2.297(0.9);2.282(0.6); 2.270(1.0); 2.266(0.9); 2.262(0.9); 2.258(0.8); 2.234(0.7);2.071 (0.7); 2.059(0.5); 2.047(0.8); 2.044(0.9); 2.036(1.1); 2.021(0.8);2.009(0.9); 1.997(0.5); 1.928(0.7); 1.915(1.0); 1.904(0.9); 1.893(1.3);1.880(1.2); 1.870(0.7); 1.858(0.7); 1.845(0.5); 1.672(0.8); 1.621(0.6);0.008(2.0); 0.000(66.8); −0.009(2.0) Compound 289a: 1H-NMR (400.0 MHz.CDCl3): δ = 7.518(15.3); 7.294(5.1); 7.260(2831.6); 7.227(5.7);7.209(4.0); 6.996(16.0); 1.537(809.6); 1.256(2.7); 0.146(3.8); 0.069(19.1); 0.008(40.2); 0.000(960.5); −0.008(36.7); −0.150(3.9) Compound296a: 1H-NMR (400.0 MHz. CDCl3): δ = 8.410(3.1); 8.403(7.8); 8.396(5.2);8.205(2.5); 7.969(4.4); 7.519(3.1); 7.373(2.2); 7.365(1.3); 7.359(1.9);7.353(1.7); 7.342 (1.5); 7.336(1.9); 7.331(1.5); 7.289(1.9); 7.283(2.1);7.278(1.7); 7.272(4.2); 7.260(579.5); 7.244(1.7); 7.227(0.9);7.209(0.9); 7.197(2.7); 7.191(2.8); 7.181(2.6); 7.175(2.6); 7.121(1.2);7.100(3.7); 7.093(2.9); 7.079(2.5); 7.072(6.5); 7.050(4.8); 7.044 (1.2);7.039(1.3); 7.033(1.1); 7.029(0.7); 7.023(0.6); 7.018(0.6); 7.011(0.6);6.996(3.3); 6.955(1.6); 6.949(1.6); 6.945(1.8); 6.939(1.6); 6.934(1.3);6.928(1.3); 6.923(1.2); 6.917(1.1); 5.299(16.0); 4.286(3.44.271(3.9);4.039(2.3); 4.022(2.5); 3.83 5(0.9); 3.814(1.0); 3.802(2.3); 3.788(2.2);3.775(2.9); 3.762(1.3); 3.713(0.6); 3.703(0.8); 3.687(1.0); 3.676(0.9);3.672(0.8); 3.662(0.7); 3.561(1.2); 3.550(1.5); 3.540(1.4); 3.535(1.3);3.529(1.5); 3.523(1.2); 3.513(1.2); 3.502(1.1); 3.440(1.1); 3.426 (1.5);3.404(1.4); 3.387(1.2); 3.374(0.9); 3.360(0.9); 3.347(0.7); 3.336(0.7);2.615(1.1); 2.289(0.42.278(0.6); 2.264(0.7); 2.254(0.9); 2.235(0.7);2.229(0.8); 2.221(0.6); 2.213(1.5); 2.200(1.5); 2.192(1.1); 2.186(1.0);2.178(1.2); 2.170(0.9); 2.164 (0.8); 2.155(0.9); 2.143(1.4); 2.131(1.3);2.120(1.7); 2.107(1.5); 2.098(0.7); 2.087(0.9); 2.071(0.8); 2.060(0.8);2.053(0.6); 2.044(0.6); 2.025(0.6); 2.005(0.6); 1.552(6.2); 1.333(0.9);1.284(1.0); 1.259(0.9); 0.146(0.6); 0.113(0.8); 0.008(6.2); 0.000(194.3); −0.009(5.5); −0.150(0.6) Compound 613a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.381(16.0); 8.369(1.42); 8.243(1.1); 8.214(15.4);7.519(5.4); 7.293(0.7); 7.289(0.8); 7.260(956.7); 7.250(5.0);7.244(2.3); 7.229(3.0); 7.226(3.7); 7.218(2.0); 7.209(3.2); 7.205(3.4);7.200(1.9); 7.185(2.0); 7.147(0.6); 7.128(1.3); 7.122(1.8); 7.118 (1.4);7.112(1.2); 7.101(1.3); 7.093(1.8); 7.087(1.4); 7.071(2.0); 7.061(1.4);7.050(3.1); 7.043(1.5); 7.030(1.9); 7.026(2.); 7.006(1.7); 6.996(5.4);6.921(1.6); 5.299(2.1); 4.265(4.0); 4.240(4.4); 4.184(3.4); 4.157(4.4);3.974(0.8); 3.965(0.8); 3.946(1.4); 3.936(1.4); 3.917(0.7); 3.908(0.6);3.887(0.8); 3.875(0.8); 3.861(1.4); 3.848(1.4); 3.836(0.9); 3.823(0.7);3.779(0.9); 3.766 (1.4); 3.753(1.8); 3.740(1.8); 3.726(1.1); 3.636(1.0);3.623(1.6); 3.610(2.0); 3.597(2.0); 3.583(1.2); 3.478(0.9); 3.467(1.1);3.456(1.2); 3.444(1.2); 3.428(1.0); 3.411(1.0); 3.399(1.1); 3.388(1.2);3.377(1.2); 3.362(0.9); 3.350(0.9); 2.544(0.6); 2.535 (0.9); 2.522(1.0);2.510(1.0); 2.499(1.3); 2.490(0.7); 2.476(0.6); 2.294(0.8); 2.266(0.9);2.231(0.7); 2.040(1.1); 2.013(0.9); 2.005(0.7); 1.936(0.7); 1.923(1.0);1.912(0.9); 1.901(1.4); 1.888(1.2); 1.878(0.7); 1.865(0.7); 1.543(11.9);1.371(0.9); 1.33 3(1.7); 1.284(2.4); 1.256(2.2); 0.146(1.0); 0.008(9.1);0.000(336.9); −0.009(9.9); −0.150(1.0) Compound 86a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.399(5.2); 8.392(5.9); 8.388(7.3); 8.381(7.3); 8.213(3.8);7.967(6.9); 7.519(1.3); 7.347(2.5); 7.342(3.2); 7.336(2.6); 7.324 (2.9);7.319(4.3); 7.313(4.2); 7.305(3.8); 7.295(5.5); 7.290(4.5); 7.285(7.2);7.280(10.6); 7.277(8.4); 7.260(230.5); 7.250 (9.2); 7.242(3.1);7.231(7.3); 7.226(3.4); 7.221(4.7); 7.216(2.8); 7.211(3.4); 7.175(1.0);7.137(4.4); 7.133(7.2); 7.128(3.9); 7.061(2.7); 7.042(2.0); 6.996(1.8);6.959(3.8); 6.940(3.4); 5.299(16.0); 4.491(0.6); 4.477(0.6); 4.278(5.6);4.263(5.8); 4.038 (3.3); 4.021(3.5); 3.835(1.0); 3.802(1.5); 3.789(3.1);3.776(3.2); 3.762(3.8); 3.749(1.9); 3.695(0.9); 3.684(1.4); 3.669(1.6);3.658(1.3); 3.654(1.2); 3.643(1.2); 3.553(1.7); 3.542(2.0); 3.532(2.1);3.526(1.8); 3.520(2.1); 3.515(1.7); 3.505(1.6); 3.493(2.0); 3.473(0.9);3.463(2.2); 3.447(2.7); 3.437(2.1); 3.425(2.2); 3.408(1.1); 3.389(1.0);3.377(1.0); 3.365(1.3); 3.353(1.3); 3.339 (0.9); 3.327(0.8); 2.964(0.8);2.945(0.8); 2.911(0.5); 2.315(0.5); 2.300(0.6); 2.291(0.9); 2.281(1.0);2.266(1.0); 2.255(1.4); 2.240(1.4); 2.232(1.3); 2.225(0.9); 2.218(2.1);2.204(2.5); 2.196(1.5); 2.190(1.5); 2.183(1.9); 2.168(1.2); 2.158(1.3);2.145 (2.3); 2.134(2.0); 2.122(2.7); 2.110(2.5); 2.099(1.8); 2.087(1.4);2.074(1.4); 2.065(0.9); 2.048(0.6); 2.037(0.8); 1.570(1.7); 1.371(1.1);1.333(0.9); 1.286(1.7); 1.257(2.5); 0.880(0.5); 0.008(3.5); 0.000(88.5);−0.009(3.7) Compound 619 bab: 1H-NMR (400.0 MHz. CDCl3): δ = 8.421(9.4);8.250(10.9); 7.595(1.5); 7.590(1.6); 7.580(1.5); 7.574(1.5); 7.417(1.6);7.411(1.7); 7.401(1.6); 7.396(1.6); 7.328 (0.7); 7.322(0.7); 7.317(0.8);7.311(0.7); 7.307(1.1); 7.301(1.1); 7.296(1.1); 7.290(1.0); 7.261(61.7);7.217(1.9); 7.196(2.6); 7.176(1.3); 7.113(0.7); 7.107(0.7); 7.102(0.8);7.096(0.8); 7.092(1.1); 7.086(1.1); 7.081(1.1); 7.075(0.9); 7.019(2.2);6.999 (3.0); 6.978(1.4); 4.267(0.6); 4.254(1.3); 4.239(1.2); 4.225(1.7);4.216(2.4); 4.190(2.5); 4.164(2.5); 4.136(3.1); 4.117(1.3); 4.102(1.2);4.088(1.5); 4.075(0.9); 4.046(0.9); 4.034(1.0); 4.024(1.1); 4.017(0.9);4.012(1.0); 4.006(0.8); 3.995(0.7); 3.983 (0.7); 3.961(16.0);3.926(14.2); 3.908(0.8); 3.901(0.7); 3.896(0.8); 3.890(0.6);3.879(0.43.868(0.6); 3.845(0.6); 3.836(0.6); 3.817(1.0); 3.807(1.0);3.789(0.5); 3.779(0.5); 3.769(0.5); 3.741(0.8); 3.731(0.8); 2.682(0.6);2.669(0.8); 2.659(0.8); 2.646 (0.8); 2.637(0.5); 2.464(0.5); 2.437(0.6);2.183(0.6); 2.015(0.6); 2.004(0.6); 1.992(0.7); 1.980(0.7); 1.586(0.6);1.255(0.7); 0.008(0.8); 0.000(23.4); −0.008(0.8) Compound 599 bae:1H-NMR (400.0 MHz. CDCl3): δ = 8.409(5.4); 8.215(5.9); 7.400(1.0);7.396(2.3); 7.394(2.0); 7.392(1.5); 7.378(3.0); 7.274(0.8); 7.269(1.2);7.261(39.2); 7.252 (1.0); 7.247(0.6); 7.242(0.5); 7.240(0.5);7.237(0.6); 7.226(0.7); 7.222(1.0); 7.221(1.3); 7.217(1.1); 7.196(2.7);7.177(1.7); 7.157(0.7); 7.052(0.9); 7.033(0.7); 4.214(1.4); 4.206(0.7);4.188(1.8); 4.177(0.9); 4.163(1.7); 4.135(1.7); 4.058(0.6); 4.043 (0.6);4.029(1.2); 4.016(0.7); 3.922(8.4); 3.889(0.5); 3.882(4.2); 3.878(4.3);3.849(0.5); 3.822(0.5); 3.812(0.5); 3.407(16.0); 3.387(14.7);0.000(14.8) Compound 289a threo-1: 1H-NMR (400.0 MHz. CDCl3): δ =8.395(14.8); 8.389(14.9); 8.193(14.6); 7.521(1.2); 7.295(0.8);7.285(0.6); 7.284(0.6); 7.283(0.6); 7.2823(0.5); 7.2815(0.5);7.281(0.6); 7.2783(0.9); 7.2775(0.9); 7.277(1.0); 7.276(1.2);7.272(6.5); 7.2663(10.5); 7.2655(11.5); 7.262 (205.0); 7.256(2.0);7.255(1.7); 7.254(1.5); 7.253(1.4); 7.252(1.4); 7.249(5.9); 7.244(7.3);7.238(5.5); 7.155(5.5); 7.134(9.2); 7.131(6.3); 7.114(7.2); 7.110(9.2);7.089(6.6); 7.083(5.1); 7.077(5.3); 7.065(5.2); 7.059(6.1); 7.057(6.0);7.050(5.4); 7.038 (4.9); 7.032(5.1); 6.998(1.2); 6.923(3.3); 6.918(4.3);6.913(6.2); 6.908(4.4); 6.902(4.4); 6.897(3.7); 6.892(5.0); 6.887(3.5);6.882(2.5); 5.299(8.7); 4.045(15.0); 4.027(16.0); 3.708(4.0);3.698(4.8); 3.694(4.9); 3.682(6.6); 3.671(5.8); 3.667(5.6); 3.657 (4.8);3.482(2.7); 3.472(2.9); 3.464(2.8); 3.454(5.3); 3.445(3.1); 3.437(2.9);3.427(2.6); 3.391(4.8); 3.380(5.6); 3.367(6.2); 3.365(5.4); 3.356(6.1);3.353(5.8); 3.341(4.8); 3.329(4.4); 2.323(2.1); 2.313(2.3); 2.309(2.5);2.299(4.3); 2.288(4.4); 2.285 (2.9); 2.278(3.4); 2.274(4.4); 2.264(5.6);2.254(3.1); 2.250(2.9); 2.240(2.6); 2.096(2.7); 2.085(5.0); 2.074(2.9);2.068(2.8); 2.058(5.3); 2.050(4.3); 2.047(3.4); 2.039(2.1); 2.033(2.2);2.022(3.7); 2.011(1.9); 1.592(5.5); 1.333(1.0); 1.284(1.4); 1.255 (1.6);0.008(2.0); 0.000(66.6); −0.009(2.0) Compound 512a: 1H-NMR (400.0 MHz.CDCl3): δ = 8.564(1.2); 8.544(11.3); 8.529(3.7); 8.495(16.0);8.471(1.0); 8.440(0.7); 8.425(1.0); 8.412(7.1); 8.400(7.1); 8.393(2.6);8.381(2.6); 8.372(10.3); 8.360(10.3); 7.521(0.9); 7.500(4.9);7.495(5.3); 7.484(5.1); 7.478(5.3; 7.453(3.8); 7.447(4.1); 7.436 (3.9);7.430(4.1); 7.373(0.8); 7.333(3.3); .327(3.3); 7.322(3.5); 7.316(3.6);7.311(4.6); 7.305(4.5); 7.300(4.5); 7.294(4.6); 7.286(3.0); 7.281(3.3);7.275(3.5); 7.270(5.2); 7.262(109.3); 7.254(4.7); 7.242(1.5);7.219(6.0); 7.202(11.1); 7.198(12.8); 7.187(8.0); 7.181(12.3);7.176(4.7); 7.160(5.4); 7.127(0.7); 7.105(8.9); 7.092(8.6); 6.998(0.8);5.299(5.0); 4.417(7.0); 4.402 (7.1); 4.052(5.4); 4.034(5.5); 3.868(0.5);3.851(0.5); 3.811(3.1); 3.801(3.1); 3.784(3.4); 3.773(3.4); 3.727(0.5);3.690(13.9); 3.564(3.2); 3.546(3.4); 3.537(5.8); 3.519(6.0); 3.501(3.9);3.489(4.1); 3.481(6.1); 3.472(8.7); 3.462(3.5); 3.454(3.5); 3.445 (3.1);3.090(1.7); 3.071(3.2); 3.051(2.1); 3.021(3.2); 3.011(3.4); 2.987(4.8);2.977(4.8); 2.885(1.8); 2.866(5.4); 2.852(4.7); 2.838(5.9); 2.827(7.5);2.811(5.2); 2.804(4.4); 2.792(1.7); 2.777(1.4); 2.702(2.3); 2.683(3.6);2.664(1.9); 2.494(0.9); 2.483 (1.5); 2.470(2.0); 2.465(1.9); 2.460(2.2);2.451(2.2); 2.446(1.9); 2.441(2.4); 2.430(2.3); 2.422(2.0); 2.413(2.7);2.404(2.5); 2.397(2.6); 2.387(2.4); 2.379(1.5); 2.370(1.3); 2.360(0.7);1.840(1.0); 1.255(0.5); 0.008(1.6); 0.000(40.9); −0.009(1.7) Example1808(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 7.835(12.2); 7.822(15.8);7.520(1.4); 7.301(3.3); 7.295(3.3); 7.290(0.7); 7.284(3.4); 7.278(3.9);7.261(251.6); 7.254(6.1); 7.248(5.0); 7.237(4.5); 7.231(4.6);7.128(5.3); 7.107(14.7); 7.086(1.0); 7.078(2.8); 7.072(2.5); 7.066(2.8);7.061(2.6); 7.056 (1.4); 7.050(1.3); 7.044(3.7); 7.039(3.6); 7.033(3.1);7.027(2.8); 7.023(1.9); 7.016(1.8); 7.012(1.7); 7.006(1.6); 6.997(1.5);6.923(0.5); 6.852(16.0); 6.835(11.7); 4.225(6.0); 4.210(6.2);4.133(4.8); 4.114(5.1); 3.813(1.7); 3.801(3.9); 3.787(3.6); 3.774 (4.8);3.761(2.4); 3.757(1.6); 3.746(1.8); 3.743(1.7); 3.730(2.1); 3.719(2.1);3.716(2.0); 3.705(1.6); 3.621(1.6); 3.601(3.4); 3.595(2.6); 3.589(4.9);3.582(3.9); 3.573(4.2); 3.571(3.5); 3.563(3.3); 3.557(2.9); 3.547(2.4);3.544(1.7); 3.530(1.9); 3.491 (1.7); 3.480(1.9); 3.467(2.0); 3.464(1.7);3.456(2.0); 3.453(1.8); 3.440(1.6); 3.429(1.5); 2.232(0.6); 2.222(0.6);2.218(0.7); 2.208(1.3); 2.197(1.5); 2.187(1.3); 2.183(1.4); 2.173(2.2);2.163(1.2); 2.159(1.2); 2.149(1.0); 2.119(3.8); 2.112(1.6); 2.105 (6.0);2.100(7.1); 2.091(3.3); 2.087(7.1); 2.074(2.8); 2.070(3.5); 2.067(1.9);2.064(1.6); 2.056(0.7); 2.050(0.8); 2.039(1.3); 2.028(0.6); 1.528(1.8);0.008(3.1); 0.000(98.2); −0.009(3.0) Example 1774(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.741(9.4); 8.726(15.0); 8.004(1.0); 7.586(9.7);7.467(16.0); 7.265(66.6); 7.160(1.7); 7.142(3.3); 7.139(3.3);7.135(2.1); 7.121(5.3); 7.118(5.3); 7.115(3.4); 7.101(3.9); 7.097(5.3);7.094(4.0); 7.087(2.0); 7.076(4.2); 7.069(2.1); 7.061(1.8); 7.048 (1.6);7.043(1.6); 7.010(2.5); 7.004(2.7); 6.992(2.6); 6.986(3.3); 6.977(2.8);6.965(2.6); 6.960(3.7); 6.950(2.1); 6.946(1.5); 6.940(1.5); 6.934(1.2);6.929(1.6); 6.925(1.2); 6.920(0.8); 6.893(1.8); 6.889(2.4); 6.884(3.1);6.879(2.4); 6.873(2.4); 6.868 (2.1); 6.863(2.6); 6.858(1.9); 6.853(1.3);4.293(7.5); 4.279(7.8); 4.041(4.7); 4.024(5.4); 3.834(2.2); 3.822(5.2);3.816(1.8); 3.808(5.2); 3.795(7.2); 3.786(5.0); 3.782(4.4); 3.777(3.1);3.771(3.1); 3.763(3.9); 3.749(3.1); 3.739(1.7); 3.735(1.7); 3.725 (1.8);3.722(2.0); 3.712(1.9); 3.708(1.9); 3.698(1.6); 3.603(2.7); 3.592(3.1);3.581(3.1); 3.576(2.6); 3.570(3.2); 3.565(2.6); 3.554(2.4); 3.543(2.3);3.483(3.6); 3.469(1.6); 3.458(1.8); 3.445(2.1); 3.443(1.9); 3.434(2.1);3.432(1.9); 3.418(1.6); 3.407 (1.4); 2.958(8.7); 2.880(7.4); 2.879(7.4);2.352(0.7); 2.343(0.8); 2.338(0.8); 2.328(1.5); 2.318(1.5); 2.314(1.0);2.308(1.1); 2.304(1.5); 2.293(1.8); 2.284(1.0); 2.279(1.0); 2.274(1.1);2.270(1.0); 2.261(1.4); 2.252(1.1); 2.247(1.2); 2.238(3.0); 2.225 (3.4);2.217(2.1); 2.212(1.9); 2.203(2.5); 2.190(1.6); 2.158(1.7); 2.147(2.5);2.135(3.1); 2.123(3.3); 2.111(2.9); 2.099(1.8); 2.088(1.3); 2.076(0.9);2.013(0.9); 2.003(1.6); 1.993(0.9); 1.985(1.0); 1.975(1.7); 1.968(1.5);1.965(1.2); 1.958(0.8); 1.951 (0.8); 1.940(1.3); 1.930(0.7); 1.816(4.8);0.008(0.9); 0.000(25.3); −0.009(0.8) Example 192(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.579(6.2(1b8.575(6.5); 8.568(6.5); 8.564(6.4);8.524(6.7); 8.520(6.8); 8.512(6.9); 8.508(6.8); 7.734(7.2); 7.730(7.3);7.714 (7.9); 7.710(7.7); 7.525(8.3); 7.521(8.4); 7.519(2.9); 7.505(9.2);7.501(8.9); 7.383(2.3); 7.368(2.5); 7.363(4.5); 7.349(4.6); 7.343(3.3);7.329(3.1); 7.293(0.6); 7.260(329.1); 7.225(8.3); 7.214(8.2);7.205(10.0); 7.194(7.9); 7.190(3.1); 7.185(5.3); 7.170(9.4); 7.165(4.2);7.155(3.4); 7.150(6.8); 7.107(3.1); 7.104(12.0); 7.097(3.5); 7.092(9.6);7.084(10.9); 7.079(4.5); 7.072 (12.1); 7.068(2.3); 7.066(2.0);7.053(4.5); 7.051(4.4); 7.047(3.4); 7.045(3.0); 7.033(2.3); 7.030(2.2);7.026(1.7); 7.024 (1.6); 6.996(1.9); 6.971(3.9); 6.968(5.1); 6.965(4.7);6.952(3.4); 6.948(4.3); .946(3.8); 6.926(2.1); 6.924(2.1); 6.920(2.7);6.918(2.5); 6.905(3.4); 6.903(3.5); 6.899(4.7); 6.897(4.3); 6.884(2.0);6.880(4.5); 6.875(6.2); 6.869(2.5); 6.856(3.7); 6.852 (4.1); 6.846(2.4);4.395(7.9); 4.370(16.0); 4.346(8.9); 4.181(2.7); 4.170(5.1); 4.157(5.1);4.146(8.8); 4.135(5.1); 4.121(4.4); 4.111(2.1); 3.630(2.1); 3.615(3.1);3.602(5.5); 3.588(4.9); 3.574(3.2); 3.499(4.6); 3.485(6.0); 3.480(3.8);3.471(5.8); 3.466 (4.2); 3.457(6.9); 3.452(2.9); 3.442(3.3); 3.438(2.7);3.399(3.3); 3.385(3.7); 3.379(3.8); 3.371(2.2); 3.366(3.6); 3.358(2.2);3.352(2.3); 3.338(2.0); 2.467(0.6); 2.454(1.42); .440(0.8); 2.433(2.5);2.419(4.4); 2.413(2.8); 2.410(3.2); 2.406(2.9); 2.402 (3.3); 2.396(5.1);2.387(3.1); 2.383(4.7); 2.378(2.8); 2.368(2.6); 2.359(0.8); 2.348(0.5);2.344(0.7); 2.105(1.2); 2.091(2.3); 2.081(1.3); 2.078(1.4); 2.071(1.8);2.067(2.4); 2.057(3.2); 2.047(1.7); 2.043(1.6); 2.033(3.0); 2.019(1.4);2.005(0.6); 1.873 (1.5); 1.858(1.7); 1.854(1.7); 1.848(1.8); 1.843(1.9);1.839(2.6); 1.828(2.6); 1.824(1.5); 1.819(1.5); 1.813(1.3); 1.809(1.4);1.804(1.2); 1.793(1.2); 1.622(4.0); 0.008(3.8); 0.000(122.5);−0.009(3.6) Example 215(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.577(10.7); 8.573(11.0); 8.565(11.1); 8.562(10.9); 8.524(6.5);8.520(6.7); 8.512(6.8); 8.509(6.5); 7.729(11.1); 7.725(11.2);7.708(12.4); 7.705(11.8); 7.539(8.0); 7.535(7.9); 7.518(15.9);7.515(8.7); 7.414(8.9); 7.409(9.8); 7.398(9.1); 7.392(9.5); 7.359(1.4);7.292(2.8); 7.260(1373.1); 7.251(10.7); 7.245(7.0); 7.239(5.8);7.235(7.8); 7.227(15.1); 7.224(8.3); 7.216(14.9); 7.210(5.7);7.207(12.2); 7.196(13.8); 7.192(6.9); 7.181(6.4); 7.175(6.8);7.166(13.1); 7.158(1.8); 7.145(21.2); 7.124(8.8) 7.115(9.4); 7.103(9.0);7.094(8.5); 7.083(8.6); 7.046(2.6); 7.040(2.5); 7.035(2.9); 7.029(2.6);7.025(4.6); 7.019(4.5); 7.013 (4.6); 7.008(4.4); 6.996(8.2); 6.984(8.8);6.963(12.5); 6.942(4.6); 6.914(1.0); 4.362(13.3); 4.357(9.1);4.338(16.0); 4.332 (10.9); 4.163(2.9); 4.144(7.3); 4.133(5.4);4.128(3.7); 4.120(10.4); 4.109(8.1); 4.103(2.9); 4.096(3.7); 4.085(3.6);3.637(2.4); 3.623(4.6); 3.609(5.6); 3.596(6.3); 3.581(3.2); 3.524(3.3);3.510(6.7); 3.496(7.6); 3.492(4.3); 3.482(10.3); 3.476(5.7); 3.468(5.7); 3.458(3.7); 3.448(3.5); 3.430(2.6); 3.415(5.5); 3.401(6.5);3.395(6.4); 3.387(3.9); 3.382(6.1); 3.374(3.9); 3.367 (4.42); .354(3.6);2.413(4.9); 2.398(7.4); 2.382(6.8); 2.379(8.4); 2.365(4.9); 2.110(1.9);2.097(3.6); 2.087(2.2); 2.073(4.2); 2.062(5.0); 2.052(2.8); 2.038(4.6);2.025(2.2); 2.005(2.4); 1.882(2.8); 1.870(3.1); 1.866(3.3); 1.862(3.3);1.855(3.1); 1.851 (3.6); 1.847(4.9); 1.836(4.7); 1.832(2.8); 1.827(2.8);1.821(2.6); 1.816(2.5); 1.801(2.0); 1.587(6.3); 0.157(2.0); 0.146(1.6);0.008(16.7); 0.000(516.3); −0.009(15.4); −0.050(1.6); −0.149(1.6)Example 1484(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.003(1.8);7.301(2.2); 7.295(2.4); 7.284(2.4); 7.279(2.3); 7.263(50.3); 7.220(4.5);7.214(4.8); 7.203(4.6); 7.197(4.6); 7.131 (1.3); 7.110(6.2);7.089(14.8); 7.083(2.2); 7.077(2.4); 7.068(7.4); 7.062(0.8); 7.056(0.6);7.050(0.6); 7.019(3.1); 7.014 (3.1); 7.009(3.5); 7.000(6.4); 6.997(6.9);6.992(2.2); 6.987(2.1); 6.981(2.0); 6.973(11.3); 6.969(11.7);6.718(14.0); 6.717 (14.2); 6.715(14.3); 4.190(6.7); 4.176(7.0);4.010(3.4); 3.993(3.7); 3.813(1.8); 3.801(4.0); 3.787(3.7); 3.774(5.2);3.761(2.5); 3.750(0.9); 3.741(1.1); 3.736(1.1); 3.724(1.4); 3.714(1.3);3.709(1.3); 3.699(1.1); 3.623(2.4); 3.612(2.7); 3.602(2.8); 3.596 (2.2);3.590(2.8); 3.585(2.2); 3.575(2.6); 3.564(2.9); 3.556(1.0); 3.546(3.2);3.532(3.6); 3.522(2.5); 3.517(3.5); 3.508(3.8); 3.493(3.1); 3.484(15.8);3.479(1.4); 3.466(1.1); 3.454(1.0); 2.958(16.0); 2.880(13.6);2.879(13.4); 2.279(0.5); 2.270(0.6); 2.264(0.6); 2.255(1.1); 2.244(0.9);2.240(0.6); 2.235(0.8); 2.230(0.9); 2.220(1.3); 2.211(0.7); 2.205(0.6);2.196(0.6); 2.189 (0.7); 2.176(1.2); 2.168(0.7); 2.163(0.9); 2.154(2.6);2.141(3.5); 2.133(2.0); 2.127(1.8); 2.119(2.9); 2.114(1.8); 2.106(1.9);2.102(3.3); 2.090(3.1); 2.078(3.4); 2.066(2.6); 2.054(1.2); 2.042(1.2);2.030(0.6); 2.018(0.6); 2.007(1.0); 1.996(0.7); 1.989 (0.6); 1.983(0.7);1.979(1.1); 1.972(0.9); 1.968(0.7); 1.954(0.5); 1.944(0.8); 1.496(6.6);0.008(0.6); 0.000(19.0) Example 127 threo: ¹H-NMR (600.1 MHz. CDCl₃): δ= 7.660(1.8); 7.648(3.2); 7.635(2.0); 7.444(0.5); 7.432(0.4);7.282(3.0); 7.269(3.4); 7.261(50.0); 7.211(3.3); 7.205(1.1); 7.199(3.4);7.194(1.7); 7.189(1.4); 7.183(1.9); 7.180(1.6); 7.175(0.9); 7.172(0.9);7.166(1.2); 7.152(0.4); 7.088(1.1); 7.084(1.2); 7.074(0.9); 7.017(0.3);7.001(0.4); 6.819(0.4); 6.806(0.4); 4.362(0.4); 4.345(0.4); 4.270(2.7);4.254(2.8); 3.555(0.); 3.548(1.0); 3.538(1.4); 3.529(1.2); 3.520(0.8);3.456(0.7); 3.449(0.8); 3.439(1.4); 3.432(1.3); 3.422(0.9); 3.415(0.7);3.304(0.8); 3.296(0.9); 3.288 (1.1); 3.286(0.9); 3.280(1.0); 3.278(0.9);3.270(0.8); 3.262(0.7); 2.003(0.4); 1.995(0.7); 1.987(0.5); 1.978(0.8);1.972(1.0); 1.964(0.6); 1.955(0.8); 1.947(0.4); 1.771(0.4); 1.764(0.5);1.761(0.5); 1.755(0.8); 1.748(0.8); 1.739(0.8); 1.732(0.6); 1.725 (0.5);1.723(0.4); 1.716(0.3); 1.528(4.5); 0.005(0.8); 0.000(14.4); −0.006(0.5)Example 127 erythro: ¹H-NMR (600.1 MHz. CDCl₃): δ = 7.457(1.2);7.444(2.2); 7.431(1.4); 7.261(50.0); 7.166(2.0); 7.152(1.8); 7.032(0.5);7.017(1.5); 7.004(1.4); 7.01(1.7); 6.995 (0.6); 6.987(1.0); 6.983(0.5);6.864(0.8); 6.857(0.6); 6.850(0.6); 6.819(1.9); 6.807(1.8); 4.362(1.8);4.346(1.9); 3.701(0.5); 3.694(0.7); 3.691(0.6); 3.684(0.8); 3.675(0.7);3.673(0.7); 3.666(0.5); 3.445(0.5); 3.440(0.5); 3.428(0.9); 3.423(0.9);3.410 (0.5); 3.405(0.5); 3.351(0.5); 3.343(0.6); 3.335(0.8); 3.327(0.8);3.317(0.5); 3.309(0.5); 2.404(0.5); 2.397(0.5); 2.388(0.5); 2.381(0.6);2.375(0.4); 2.371(0.3); 2.271(0.3); 2.263(0.6); 2.256(0.4); 2.252(0.4);2.245(0.7); 2.240(0.6); 2.222(0.4); 1.546 (10.9); 0.005(0.7);0.000(14.2) Example 1758(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.730(9.1); 8.710(15.1); 8.004(0.7); 7.588(9.6); 7.449(16.0);7.334(1.6); 7.319(1.8); 7.312(3.8); 7.297(4.1); 7.291(5.1); 7.277(5.2);7.271(4.2); 7.265(70.6); 7.257(3.8); 7.049(1.2); 7.047(1.4); 7.043(1.4);7.041(1.6); 7.032(2.2); 7.030(2.6); 7.026 (4.7); 7.022(3.0); 7.020(3.3);7.011(6.1); 7.009(7.3); 7.005(6.1); 7.003(4.9); 6.999(2.0); 6.991(4.6);6.984(2.2); 6.982(2.1); 6.975(2.3); 6.970(2.5); 6.964(1.5); 6.952(2.2);6.946(2.7); 6.941(4.6); 6.940(4.7); 6.937(5.2); 6.935(4.8); 6.919(3.6);6.918 (4.6); 6.916(4.4); 6.892(3.3); 6.887(4.1); 6.881(2.5); 6.869(3.2);6.863(4.1); 6.858(2.5); 4.300(8.2); 4.286(8.6); 4.063(4.9); 4.046(5.7);3.842(1.2); 3.833(1.5); 3.826(2.9); 3.823(3.2); 3.813(5.7); 3.810(6.6);3.804(3.6); 3.797(6.5); 3.789(5.0); 3.783 (6.5); 3.775(2.2); 3.770(3.0);3.730(1.3); 3.720(1.6); 3.716(1.6); 3.704(2.0); 3.693(1.9); 3.689(1.8);3.679(1.6); 3.596(2.7); 3.585(3.1); 3.575(3.1); 3.569(2.6); 3.563(3.2);3.558(2.6); 3.548(2.5); 3.536(2.3); 3.481(4.2); 3.458(1.6); 3.447(1.8);3.434 (2.1); 3.432(1.7); 3.423(2.0); 3.420(1.8); 3.407(1.6); 3.396(1.4);2.9563(6.8); 2.9558(6.7); 2.879(5.8); 2.878(5.8); 2.354(0.7);2.345(0.8); 2.339(0.8); 2.330(1.6); 2.319(1.3); 2.315(0.9); 2.310(1.1);2.305(1.3); 2.295(1.9); 2.286(1.0); 2.280(1.1); 2.277 (1.2); 2.271(1.0);2.263(1.7); 2.255(1.1); 2.250(1.2); 2.242(3.3); 2.228(3.8); 2.220(2.1);2.215(1.9); 2.206(2.8); 2.193(1.6); 2.157(1.7); 2.146(2.7); 2.134(3.2);2.122(3.6); 2.110(3.1); 2.098(1.8); 2.086(1.5); 2.074(0.9); 2.027(0.9);2.017(1.4); 2.006 (1.0); 1.999(0.9); 1.992(1.0); 1.989(1.5); 1,982(1.3);1.978(1.1); 1.971(0.8); 1.964(0.8); 1.954(1.2); 1.943(0.7); 1.808(3.8);0.008(0.8); 0.000(27.4); −0.009(0.8) Example 181(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.523(3.7); 8.520(1.5); 8.517(1.6); 8.513(3.7);8.481(5.3); 8.472(5.3); 7.263(50.0); 7.259(12.4); 7.200(1.1);7.186(2.3); 7.180(1.4); 7.176(1.); 7.170(2.8); 7.166(4.8); 7.162(5.3);7.157(5.1); 7.154(4.); 7.147(1.2); 7.086(0.3); 7.063(1.6); 7.061 (1.3);7.057(1.2); 7.046(2.2); 7.032(2.7); 7.016(2.6); 7.002(1.5); 6.990(1.4);6.987(1.5); 6.978(1.5); 6.974(2.0); 6.969(1.5); 6.960 (1.4); 6.957(1.4);6.930(6.1); 6.927(5.8); 6.866(1.9); 6.863(1.6); 6.859(1.5); 6.852(1.6);4.381(4.8); 4.364(5.0); 4.317(3.8); 4.301(3.9); 3.684(1.3); 3.677(1.8);3.675(1.8); 3.667(2.2); 3.658(2.1); 3.657(2.0); 3.649(1.5); 3.563(1.0);3.554(1.7); 3.545 (2.1); 3.536(2.0); 3.527(1.2); 3.488(4.1); 3.458(1.0);3.451(1.1); 3.42(2.0); 3.435(2.4); 3.426(1.3); 3.420(2.9); 3.415(2.5);3.404(1.4); 3.398(1.3); 3.377(1.5); 3.370(1.7); 3.361(2.0); 3.359(1.8);3.354(2.0); 3.352(1.8); 3.343(1.5); 3.336(1.4); 3.330 (1.2); 3.322(1.3);3.315(1.4); 3.312(1.3); 3.307(1.4); 3.304(1.3); 3.297(1.2); 3.289(1.0);2.403(0.6); 2.397(0.7); 2.393(0.7); 2.387(1.2); 2.380(1.3); 2.371(1.3);2.364(1.6); 2.358(1.0); 2.354(0.9); 2.349(0.8); 2.261(0.9); 2.254(1.7);2.246(1.0); 2.243 (1.0); 2.236(1.9); 2.230(1.6); 2.223(0.7); 2.220(0.7);2.213(1.2); 2.205(0.6); 2.001(0.7); 1.994(1.2); 1.985(1.2); 1.977(1.7);1.970(2.0); 1.962(1.7); 1.953(2.1); 1.945(1.7); 1.915(2.2); 1.833(0.9);1.825(1.1); 1.817(1.2); 1.810(1.4); 1.801(1.4); 1.794 (0.9); 1.787(0.8);1.778(0.6); 0.005(0.6); 0.000(12.8); −0.006(0.5) Example 1515(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 7.361(0.5); 7.351(0.7); 7.348(1.0);7.338(2.5); 7.328(2.1); 7.324(3.6); 7.315(3.2); 7.311(2.1); 7.301(1.9);7.291(4.1); 7.262 (50.0); 7.114(12.4); 7.092(0.4); 7.085(0.3);7.072(0.5); 7.068(0.6); 7.058(1.0); 7.052(1.8); 7.047(1.8); 7.036(3.3);7.033(4.1); 7.019(2.6); 7.010(0.8); 7.007(1.0); 6.995(0.48); 6.992(1.0);6.969(3.8); 6.956(3.5); 6.930(2.2); 6.927(3.0); 6.914(2.2); 6.911 (2.9);4.280(5.6); 4.271(5.7); 4.061(1.8); 4.050(1.9); 3.851(1.5); 3.843(3.0);3.834(2.9); 3.825(3.5); 3.816(1.7); 3.761(0.6); 3.755(1.0); 3.749(1.1);3.739(2.5); 3.730(3.8); 3.723(2.5); 3.714(2.9); 3.705(1.4); 3.640(1.7);3.633(1.9); 3.625(2.1); 3.622 (1.9); 3.618(2.1); 3.615(1.8); 3.607(1.6);3.600(1.5); 3.495(0.6); 3.490(2.8); 3.478(0.9); 3.471(0.9); 3.460(0.5);3.453(0.5); 2.259(0.5); 2.252(0.6); 2.243(0.6); 2.236(0.6); 2.230(1.0);2.221(1.4); 2.215(0.9); 2.212(0.9); 2.207(2.1); 2.198(2.3); 2.192 (1.3);2.189(1.2); 2.183(1.7); 2.174(0.9); 2.110(1.0); 2.103(1.7); 2.095(1.9);2.087(2.3); 2.079(2.1); 2.071(1.3); 2.064(1.1); 2.055(0.6); 1.939(0.5);1.932(0.3); 1.928(0.3); 1.921(0.6); 1.916(0.6); 1.897(0.5); 1.556(7.6);0.000(14.4); −0.006(0.5) Example 1461(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 8.004(1.0); 7.343(1.1); 7.328(1.4); 7.324(3.8); 7.309(4.0);7.304(5.0); 7.289(4.9); 7.284(3.1); 7.269(3.2); 7.261(50.1); 7.054(0.9); 7.052(1.1); 7.047(1.1); 7.045(1.5); 7.043(1.9); 7.041(2.0);7.036(2.1); 7.034(2.6); 7.031(2.5); 7.027(3.6); 7.024(4.7); 7.022(5.5);7.020(4.4); 7.016(3.6); 7.013(3.8); 7.009(2.2); 7.004(3.9); 7.001(2.8);6.999(2.0); 6.995(1.9); 6.992(2.1); 6.988 (6.3); 6.985(7.2); 6.982(2.3);6.976(1.2); 6.963(2.1); 6.956(15.1); 6.952(16.0); 6.934(3.7);6.933(3.5); 6.904(2.7); 6.899 (3.4); 6.893(2.1); 6.880(2.7); 6.875(3.3);6.870(2.1); 6.727(5.1); 6.726(5.0); 6.724(5.1); 6.722(4.8); 6.708(9.2);6.707(9.3); 6.704(9.4); 4.202(6.9); 4.187(7.2); 4.043(3.7); 4.026(4.0);3.800(1.8); 3.787(3.43.774(3.8); 3.761(4.9); 3.748(2.4); 3.733 (1.0);3.724(1.2); 3.719(1.2); 3.707(1.7); 3.697(1.5); 3.692(1.4); 3.682(1.2);3.614(2.4); 3.603(2.7); 3.593(3.6); 3.587(2.5); 3.581(4.9); 43.576(3.3);3.566(6.3); 3.554(4.4); 3.543(3.5); 3.528(1.7); 3.508(1.7); 3.496(1.5);3.484(10.9); 3.472(1.6); 3.469 (1.4); 3.457(1.2); 3.445(1.1);2.956(9.3); 2.879(7.42.878(7.6); 2.281(0.6); 2.272(0.6); 2.266(0.6);2.258(1.2); 2.247(0.9); 2.243(0.7); 2.238(0.8); 2.232(0.9); 2.223(1.5);2.214(0.8); 2.208(0.7); 2.199(0.7); 2.187(0.7); 2.174(1.3); 2.166(0.7);2.161 (0.9); 2.152(2.7); 2.139(3.7); 2.131(2.0); 2.125(1.8);2.118(3.42.111(1.8); 2.104(1.8); 2.099(3.4); 2.087(3.0); 2.075(3.4);2.063(2.5); 2.052(1.2); 2.039(1.8); 2.028(1.6); 2.017(0.8); 2.010(0.7);2.004(0.7); 2.000(1.0); 1.993(0.9); 1.989(0.8); 1.982 (0.5); 1.976(0.6);1.965(0.7); 1.954(0.5); 1.449(4.9); 0.008(0.6); 0.000(19.6); −0.009(0.5)Example 1677(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.001(1.8);7.334(1.9); 7.327(3.8); 7.319(2.2); 7.312(5.7); 7.306(6.6); 7.300(4.3);7.292(6.9); 7.286(5.1); 7.279(2.8); 7.272 (5.1); 7.262(65.8);7.043(1.6); 7.040(4.0); 7.037(4.2); 7.034(4.5); 7.031(3.7); 7.019(9.5);7.016(8.0); 7.013(7.7); 7.010(6.5); 7.007(2.8); 7.006(2.9); 7.005(3.1);7.003(3.7); 7.001(4.5); 6.999(4.0); 6.998(4.2); 6.995(4.0); 6.992(3.7);6.989(3.0); 6.978 (4.9); 6.977(5.7); 6.974(9.2); 6.971(6.4); 6.964(2.2);6.958(4.9); 6.957(5.1); 6.955(6.4); 6.954(6.1); 6.953(5.9); 6.952(6.1);6.946(3.0); 6.940(1.8); 6.915(4.5); 6.910(5.5); 6.905(3.5); 6.892(4.5);6.886(5.5); 6.881(3.5); 6.394(3.5); 6.393(3.5); 6.385 (7.2); 6.383(5.0);6.380(7.1); 6.378(7.3); 6.376(5.3); 6.375(5.0); 6.370(13.2); 6.362(7.7);6.360(7.3); 6.266(12.46.261 (13.1); 6.256(11.0); 6.251(12.0);6.250(8.3); 6.245(6.7); 6.240(5.7); 6.236(5.6); 4.150(11.5);4.136(12.0); 3.992(6.1); 3.974 (6.5); 3.803(3.0); 3.790(6.3);3.776(6.6); 3.763(8.5); 3.750(5.6); 3.741(1.9); 3.736(1.9); 3.724(2.7);3.714(2.4); 3.709(2.3); 3.699(2.1); 3.641(4.2); 3.629(4.7); 3.620(4.9);3.614(3.6); 3.608(4.8); 3.602(3.5); 3.593(3.6); 3.581(3.3); 3.549(2.2);3.537 (2.5); 3.526(2.6); 3.522(2.1); 3.514(2.6); 3.510(2.2); 3.499(2.0);3.487(1.9); 3.481(6.3); 3.467(1.9); 3.461(2.6); 3.452(4.1); 3.446(4.0);3.443(3.46); .437(3.2); 3.433(3.2); 3.428(3.5); 3.422(3.7); 3.414(1.8);3.408(1.5); 2.956(16.0); 2.878(14.1); 2.877 (14.0); 2.276(0.9);2.267(0.9); 2.261(1.0); 2.252(1.8); 2.243(1.2); 2.241(1.4); 2.238(1.1);2.232(1.3); 2.229(1.2); 2.226 (1.4); 2.218(2.2); 2.209(1.2); 2.203(1.1);2.194(1.0); 2.142(1.1); 2.129(2.3); 2.121(1.2); 2.116(1.4); 2.107(4.5);2.094(6.2); 2.086 (3.3); 2.080(2.9); 2.072(5.4); 2.064(3.1); 2.059(2.9);2.052(5.8); 2.040(5.3); 2.028(5.7); 2.016(3.7); 2.004(2.2); 1.992 (2.3);1.980(1.1); 1.972(1.1); 1.960(1.6); 1.950(1.2); 1.943(1.1); 1.937(1.1);1.932(1.6); 1.925(1.4); 1.921(1.2); 1.915(0.9); 1.908(0.9); 1.898(1.2);1.886(0.8); 1.498(12.3); 0.008(0.7); 0.000(25.4); −0.009(0.7) Example1153(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.095(2.9); 8.090(5.8);8.087(3.3); 8.082(5.6); 7.264(29.0); 7.127(1.4); 7.119(0.9); 7.113(3.1);7.105(1.7); 7.097(3.0); 7.089 (1.6); 7.083(1.6); 7.075(0.7); 7.065(0.7);7.061(0.7); 7.053(0.8); 7.048(1.1); 7.043(0.8); 7.035(0.7); 7.031(0.7);7.013(1.5); 7.010(1.6); 7.001(1.7); 6.997(2.3); 6.992(1.7); 6.984(1.5);6.980(1.5); 6.914(1.0); 6.907(0.8); 6.900(0.9); 6.886(2.2); 6.879 (1.7);6.871(1.9); 6.666(2.1); 6.664(2.4); 6.658(5.6); 6.652(4.2); 6.650(3.9);6.499(3.5); 6.476(7.7); 4.192(5.3); 4.181(5.3); 4.031(0.4); 3.987(2.4);3.974(2.5); 3.912(50.0); 3.724(1.4); 3.715(2.9); 3.706(3.0); 3.698(3.3);3.689(1.6); 3.659(0.6); 3.652 (0.8); 3.649(0.8); 3.642(1.3); 3.634(0.9);3.631(0.9); 3.624(0.7); 3.494(1.7); 3.488(3.2); 3.480(1.9); 3.476(1.7);3.471(1.9); 3.468(1.7); 3.462(1.5); 3.454(1.4); 3.381(0.7); 3.373(0.8);3.365(1.0); 3.357(1.0); 3.348(0.7); 3.340(0.6); 3.278(0.7); 3.268 (1.6);3.259(3.3); 3.253(2.3); 3.248(2.2); 3.242(2.8); 3.232(1.3); 2.272(0.3);2.266(0.4); 2.262(0.4); 2.256(0.7); 2.249 (0.7); 2.240(0.7); 2.233(0.8);2.227(0.5); 2.223(0.4); 2.217(0.4); 2.110(0.6); 2.101(1.1); 2.096(0.8);2.091(1.1); 2.087(2.4); 2.077(3.6); 2.070(3.8); 2.063(6.4); 2.054(6.4);2.046(6.1); 2.038(4.2); 2.031(2.1); 2.022(2.42.014(1.1); 0.000(8.3)Example 532 threo(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.341(15.5);8.339(15.4); 8.328(16.0); 8.326(15.5); 8.308(0.8); 7.519(4.8);7.379(0.6); 7.310(1.0); 7.293(1.7); 7.260(903.9); 7.229(0.7);7.210(1.3); 7.163(5.1); 7.142(8.1); 7.138(6.3); 7.121(7.6); 7.116(20.9);7.112(19.5); 7.102(5.3); 7.097(10.7); 7.084(5.1); 7.078(5.8);7.070(5.1); 7.058(4.8); 7.052(4.9); 7.032(12.4); 7.028(11.3);7.018(11.4); 7.015(10.7); 6.996(5.2); 6.975(0.8); 6.918(3.2);6.913(4.0); 6.909(5.6); 6.904(4.3); 6.898(4.3); 6.892(3.7); 6.887(4.7);6.883(3.3); 6.877(2.4); 5.299 (4.5); 4.032(13.8); 4.014(14.6);3.709(2.1); 3.696(3.1); 3.683(4.1); 3.672(3.6); 3.658(2.6); 3.384(4.7);3.374(5.3); 3.366 (5.1); 3.356(10.5); 3.346(7.1); 3.338(5.6);3.328(5.2); 2.288(2.0); 2.278(2.2); 2.273(2.4); 2.263(4.3); 2.252(4.3);2.242(3.4); 2.238(4.3); 2.228(5.8); 2.218(3.2); 2.214(3.0); 2.204(2.6);2.170(0.6); 2.088(2.8); 2.077(5.2); 2.067(3.0); 2.061(2.7); 2.050 (5.2);2.042(4.5); 2.031(2.0); 2.025(2.2); 2.014(3.4); 2.004(1.9); 1.541(60.1);1.333(3.2); 1.284(6.3); 1.256(5.0); 0.880(0.8); 0.146(1.0); 0.008(9.2);0.000(342.5); −0.006(4.9); −0.009(11.0); −0.051(0.6); −0.150(1.1)Example 1288(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.620(14.8);8.617(14.8); 8.565(12.7); 8.562(12.6); 8.189(16.0); 8.185(15.7);8.010(0.7); 7.963(13.7); 7.960(13.4); 7.520 (1.1); 7.261(212.1);7.215(2.8); 7.211(0.6); 7.195(5.3); 7.191(3.5); 7.180(3.4); 7.174(7.3);7.170(5.7); 7.162(3.3); 7.154(4.1); 7.149(5.2); 7.135(3.0); 7.129(3.1);7.077(2.7); 7.056(4.8); 7.053(3.7); 7.046(3.1); 7.041(4.3); 7.036(6.4);7.032(6.8); 7.023 (4.7); 7.017(4.5); 7.011(4.5); 7.005(2.9); 6.997(4.1);6.991(2.8); 6.978(2.5); 6.973(2.6); 6.860(1.8); 6.856(2.2); 6.851(3.2)6.846(2.3); 6.840(2.2); 6.835(2.0); 6.829(2.5); 6.825(1.8); 6.820(1.3);4.292(9.2); 4.285(8.4); 4.270(9.6); 4.260(8.7); 3.728 (2.0); 3.717(2.8);3.701(2.9); 3.690(3.2); 3.676(2.3); 3.645(2.3); 3.633(4.5); 3.619(4.6);3.605(6.3); 3.594(6.0); 3.583(3.3); 3.577(4.0); 3.570(6.1); 3.561(3.6);3.552(2.9); 3.548(3.1); 3.543(2.5); 3.536(2.5); 3.346(2.7); 3.335(3.0);3.323(5.3); 3.319 (3.3); 3.312(5.8); 3.308(3.2); 3.297(5.0); 3.286(4.9);3.272(2.3); 3.261(2.1); 2.958(5.6); 2.882(4.8); 2.489(1.1); 2.480(1.2);2.475(1.2); 2.466(1.8); 2.454(2.0); 2.441(1.8); 2.431(2.2); 2.422(1.4);2.417(1.3); 2.408(1.1); 2.236(1.3); 2.225(2.7); 2.215 (1.5); 2.209(1.4);2.198(2.9); 2.191(2.4); 2.180(1.1); 2.174(1.1); 2.163(2.0); 2.153(0.9);2.063(1.0); 2.052(1.9); 2.040(1.5); 2.028(3.0); 2.017(3.8); 2.004(2.8);1.992(3.3); 1.980(1.6); 1.960(1.7); 1.948(2.9); 1.935(2.4); 1.925(3.6);1.913(3.1); 1.902 (1.3); 1.890(1.5); 1.878(0.9); 1.485(1.6); 0.008(2.6);0.000(79.4); −0.009(2.3) Example 1785(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 7.832(12.1); 7.818(16.0); 7.519(2.3); 7.351(0.5); 7.338(3.8);7.323(4.4); 7.317(6.8); 7.303(6.9); 7.297(5.3); 7.283(5.7); 7.260(409.8); 7.228(0.5); 7.053(1.9); 7.051(2.7); 7.047(3.2); 7.044(3.0);7.041(2.0); 7.032(3.6); 7.030(4.9); 7.026(5.9); 7.023 (5.4); 7.020(3.4);7.005(5.2); 7.002(5.8); 6.996(2.9); 6.983(3.3); 6.974(2.8); 6.968(6.0);6.951(4.6); 6.947(6.4); 6.926(3.0); 6.920(3.6); 6.915(2.2); 6.902(2.8);6.897(3.6); 6.892(2.1); 6.827(15.9); 6.821(11.6); 4.240(7.1);4.225(7.5); 4.163(5.3); 4.144 (5.6); 3.802(2.0); 3.789(4.4); 3.775(4.2);3.762(5.4); 3.749(2.6); 3.742(1.6); 3.731(1.8); 3.728(1.8); 3.716(2.4);3.704(2.2); 3.701(2.2); 3.690(1.8); 3.648(1.7); 3.632(3.2); 3.628(2.9);3.611(3.5); 3.596(3.4); 3.589(1.7); 3.580(3.9); 3.565(3.2); 3.563 (2.6);3.553(2.3); 3.547(3.0); 3.538(2.5); 3.536(1.9); 3.533(1.8); 3.520(2.2);3.487(2.0); 3.475(2.2); 3.463(2.4); 3.460(1.9); 3.452(2.3); 3.448(1.9);3.436(1.8); 3.425(1.7); 2.241(0.7); 2.231(0.8); 2.227(0.7); 2.217(1.3);2.206(1.5); 2.196(1.4); 2.19 2(1.6); 2.183(2.3); 2.173(1.3); 2.169(1.3);2.159(1.3); 2.130(1.4); 2.120(3.9); 2.109(5.7); 2.102(7.1); 2.096(3.5);2.090(7.4); 2.085(4.3); 2.074(2.9); 2.072(3.3); 2.056(1.3); 2.045(0.6);1.540(5.3); 0.157(0.6); ); 0.146(0.5); 0.008(5.3); 0.000(153.6);−0.009(4.4) Example 1801(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =7.832(12.4); 7.820(16.0); 7.265(65.4); 7.167(2.3); 7.163(1.8);7.146(4.0); 7.142(5.1); 7.138(2.2); 7.126(3.1); 7.122(5.9); 7.117(3.1);7.101(2.7); 7.097(2.2); 7.091(1.6); 7.085(1.7); 7.073(1.6); 7.067(1.9);7.065(1.9); 7.059(1.7); 7.045(2.8); 7.040 (3.0); 7.027(2.0); 7.021(2.4);7.012(2.2); 7.000(2.1); 6.994(2.1); 6.953(1.1); 6.949(1.4); 6.944(1.9);6.939(1.5); 6.933(1.4); 6.926(2.2); 6.922(3.0); 6.919(2.5); 6.916(3.2);6.912(2.3); 6.905(1.5); 6.900(1.5); 6.894(2.0); 6.890(1.5); 6.885(1.0);6.839 (15.3); 6.821(11.4); 4.238(5.9); 4.223(6.2); 4.139(4.7);4.120(5.0); 3.805(1.7); 3.792(3.8); 3.778(3.4); 3.765(4.8); 3.752(2.3);3.748(1.5); 3.737(1.7); 3.734(1.7); 3.721(2.0); 3.710(2.0); 3.707(1.9);3.696(1.6); 3.625(1.6); 3.609(2.8); 3.605(3.1); 3.598 (1.7); 3.591(3.5);3.585(3.0); 3.580(3.0); 3.572(2.3); 3.564(4.3); 3.561(2.3); 3.553(2.4);3.547(2.5); 3.537(2.5); 3.534(1.6); 3.520(1.9); 3.484(0.7); 3.481(1.7);3.470(1.9); 3.457(2.0); 3.454(1.7); 3.446(2.0); 3.443(1.8); 3.430(1.6);3.419(1.5); 2.959 (2.7); 2.881(2.3); 2.880(2.3); 2.232(0.6); 2.222(0.7);2.218(0.7); 2.209(1.3); 2.197(1.4); 2.187(1.2); 2.184(1.4); 2.174(2.1);2.164(1.1); 2.160(1.1); 2.150(1.0); 2.115(3.9); 2.108(1.6); 2.102(5.6);2.097(8.1); 2.088(2.8); 2.084(6.7); 2.080(5.3); 2.067 (3.9); 2.062(1.7);2.059(1.3); 2.051(0.7); 2.045(0.7); 2.035(1.2); 2.024(0.6); 1.685(2.4);0.008(0.8); 0.000(24.1); −0.009(0.7) Example 215(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.574(6.6); 8.570(6.9); 8.562(6.8); 8.558(6.8);8.521(6.7); 8.518(7.0); 8.510(6.9); 8.506(6.9); 8.012(0.9); 7.724(7.7);7.720 (7.8); 7.704(8.5); 7.700(8.3); 7.537(8.5); 7.533(8.6); 7.521(1.0);7.516(9.5); 7.512(9.3); 7.412(5.5); 7.406(6.0); 7.395(5.7); 7.389(5.9);7.262(113.0); 7.253(2.8); 7.247(2.4); 7.242(2.7); 7.236(2.7);7.232(4.1); 7.224(9.9); 7.221(4.6); 7.215(4.4); 7.212(9.3); 7.203(8.4);7.198(6.0); 7.192(14.0); 7.181(6.0); 7.175(6.3); 7.164(8.0);7.143(12.5); 7.121(5.1); 7.113(9.6); 7.101 (9.4); 7.092(8.8);7.081(8.6); 7.044(2.3); 7.039(2.0); 7.033(2.5); 7.027(2.4); 7.023(4.6);7.017(4.5); 7.012(4.4); 7.006(4.1); 6.998(0.8); 6.984(8.6); 6.962(12.5);6.941(4.5); 4.359(8.7); 4.355(9.2); 4.335(10.5); 4.329(11.3);4.161(2.7); 4.143(5.5); 4.136 (2.6); 4.131(3.3); 4.127(3.2); 4.118(7.4);4.108(5.1); 4.102(2.6); 4.095(2.4); 4.084(2.3); 3.632(2.1); 3.618(4.4);3.604(5.3); 3.590(6.2); 3.576(3.1); 3.522(1.9); 3.507(3.7); 3.494(4.5);3.485(16.0); 3.480(6.3); 3.470(5.4); 3.468(3.6); 3.465(3.7); 3.459(2.6);3.453(3.6); 3.443(3.6); 3.425(2.4); 3.412(3.2); 3.398(3.7); 3.392(3.8);3.384(2.3); 3.379(3.6); 3.371(2.4); 3.365 (2.4); 3.351(2.1); 2.955(9.0);2.881(7.6); 2.880(7.7); 2.410(4.9); 2.395(7.7); 2.379(6.9); 2.376(8.4);2.362(5.0); 2.108(1.1); 2.094(2.3); 2.084(1.2); 2.081(1.3); 2.073(1.9);2.071(2.5); 2.060(3.2); 2.050(1.8); 2.046(1.6); 2.036(3.0); 2.022(1.4);1.882 (1.5); 1.871(1.7); 1.867(1.8); 1.862(1.8); 1.856(1.8); 1.852(2.0);1.847(2.8); 1.837(2.7); 1.833(1.5); 1.828(1.5); 1.822(1.); 1.817(1.4);1.813(1.); 1.802(1.1); 1.629(2.8); 0.008(1.3); 0.000(42.2); −0.009(1.3)Example 1477(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.003(1.7);7.262(60.8); 7.166(1.4); 7.152(2.8); 7.145(2.5); 7.142(1.8); 7.131(4.7);7.127(3.4); 7.121(2.6); 7.111(3.5); 7.106 (4.6); 7.100(2.0); 7.097(1.6);7.091(1.6); 7.086(3.2); 7.079(1.4); 7.073(1.6); 7.071(1.5); 7.065(1.4);7.052(1.3); 7.046(1.4); 7.016(2.3); 7.010(2.5); 6.997(3.0); 6.994(7.3);6.991(9.2); 6.983(2.8); 6.971(2.9); 6.966(15.2); 6.962(14.1);6.958(2.2); 6.954(1.4); 6.947(1.2); 6.941(1.0); 6.936(1.3); 6.931(1.0);6.927(0.7); 6.903(1.7); 6.899(2.1); 6.894(2.9); 6.889(2.2); 6.883 (2.2);6.878(1.8); 6.873(2.3); 6.868(1.7); 6.863(1.2); 6.722(10.6);6.721(11.5); 6.719(11.3); 6.718(11.0); 6.715(6.8); 6.714 (6.4);6.711(6.2); 6.710(5.8); 4.199(7.1); 4.185(7.4); 4.010(3.9); 3.993(4.2);3.813(2.0); 3.800(4.4); 3.787(4.0); 3.773(5.7); 3.761 (2.7); 3.749(1.1);3.740(1.3); 3.735(1.3); 3.723(1.7); 3.713(1.6); 3.708(1.6); 3.698(1.4);3.622(2.7); 3.610(3.0); 3.601(3.1); 13.595(2.4); 3.589(3.1); 3.583(2.4);3.574(3.0); 3.567(1.4); 3.562(2.5); 3.559(1.3); 3.549(3.4); 3.536(4.0);3.526(2.6); 3.521 (3.1); 3.515(2.3); 3.512(4.1); 3.504(1.9); 3.498(2.0);3.492(2.0); 3.489(1.7); 3.485(7.5); 3.480(1.9); 3.478(1.6); 3.465 (1.4);3.454(1.3); 2.958(15.6); 2.957(16.0); 2.880(13.0); 2.878(14.0);2.288(0.6); 2.279(0.7); 2.273(0.7); 2.264(1.3); 2.253 (1.1); 2.249(0.8);2.244(0.9); 2.239(1.1); 2.229(1.6); 2.220(0.9); 2.214(0.8); 2.205(0.7);2.192(0.7); 2.178(1.2); 2.171(0.7); 2.165 (0.9); 2.156(2.9); 2.143(3.8);2.135(2.3); 2.130(2.1); 2.121(3.4); 2.107(4.4); 2.095(3.4); 2.083(3.8);2.071(2.9); 2.060 (1.3); 2.048(1.3); 2.036(0.7); 2.019(0.8); 2.008(1.2);1.998(0.8); 1.991(0.8); 1.984(0.8); 1.980(1.3); 1.974(1.1); 1.970(0.9);1.963 (0.6); 1.956(0.6); 1.946(0.9); 1.935(0.6); 1.508(3.9); 0.008(0.7);0.000(24.0); −0.009(0.7) Example 1542(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 7.996(2.0); 7.368(1.2); 7.353(1.7); 7.347(4.4); 7.332(5.0);7.327(5.9); 7.313(5.9); 7.307(3.6); 7.292(3.2); 7.266(32.8); 7.259(11.9); 7.087(20.3); 7.078(1.6); 7.076(1.6); 7.072(1.6); 7.070(1.7);7.056(4.1); 7.050(4.7); 7.036(8.47.032(6.2); 7.015(6.6); 7.010(4.4);6.991(2.4); 6.980(6.2); 6.960(4.9); 6.941(3.4); 6.936(4.3); 6.931(2.6);6.918(3.3); 6.913(4.3); 6.908(2.6); 4.294(8.1); 4.280(8.5); 4.068(4.7);4.052(5.1); 3.853(2.1); 3.840(4.3); 3.826(4.1); 3.813(5.5); 3.800(2.7);3.761(1.2); 3.751 (1.5); 3.747(1.6); 3.734(3.2); 3.724(3.1); 3.719(2.7);3.709(5.0); 3.695(4.8); 3.686(3.2); 3.681(3.8); 3.672(4.3); 3.658(2.2);3.647(2.7); 3.636(3.1); 3.625(3.1); 3.620(2.7); 3.614(3.2); 3.609(2.6);3.598(2.4); 3.587(2.2); 3.506(1.5); 3.495(1.7); 3.480 (8.0); 3.470(2.1);3.454(1.4); 3.443(1.3); 2.959(16.0); 2.877(13.6); 2.288(0.7);2.278(0.8); 2.273(0.8); 2.264(1.3); 2.253(1.4); 2.249(1.0); 2.239(2.3);2.228(2.1); 2.218(1.8); 2.212(1.6); 2.203(3.3); 2.190(3.2); 2.182(2.1);2.176(1.9); 2.168(2.3); 2.155 (1.5); 2.116(1.6); 2.104(2.4); 2.092(3.0);2.080(3.2); 2.069(2.9); 2.057(1.7); 2.046(1.3); 2.033(0.9); 1.949(0.8);1.939(1.5); 1.929(0.9); 1.922(0.9); 1.911(1.7); 1.904(1.5); 1.894(0.7);1.887(0.7); 1.876(1.2); 1.866(0.7); 1.729(4.4); 0.008(0.5); 0.000 (12.4)Example 1565(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.005(1.3);7.351(2.1); 7.345(2.2); 7.334(2.0); 7.328(2.0); 7.2724(9.5);7.2715(9.3); 7.264(57.7); 7.258(4.0); 7.252(3.7); 7.163(1.3);7.142(4.7); 7.117(17.9); 7.109(2.4); 7.103(2.1); 7.097(5.7); 7.088(0.6);7.082(0.5); 7.060(2.4); 7.054(2.3); 7.050 (2.6); 7.044(2.4); 7.039(1.5);7.033(1.5); 7.028(1.4); 7.022(1.3); 4.269(5.0); 4.255(5.2); 4.046(3.2);4.029(3.5); 3.866(1.4); 3.854(2.9); 3.840(2.7); 3.827(3.7); 3.814(1.8);3.783(0.8); 3.773(1.0); 3.769(1.0); 3.759(1.1); 3.756(1.2); 3.746(1.2);3.742 (1.2); 3.732(1.0); 3.713(0.8); 3.704(0.9); 3.697(0.8); 3.686(1.6);3.676(2.2); 3.669(1.1); 3.661(3.4); 3.658(2.8); 3.653(2.1); 3.647(3.6);3.638(3.1); 3.636(3.0); 3.630(2.0); 3.625(3.6); 3.620(1.9); 3.609(1.7);3.598(1.5); 3.521(1.1); 3.510(1.2); 3.496 (1.5); 3.487(16.0);3.469(1.0); 3.459(0.9); 2.960(11.7); 2.881(9.8); 2.880(9.9); 2.263(0.5);2.259(0.5); 2.249(0.8); 2.238(1.0); 2.232(0.9); 2.228(0.8); 2.224(1.1);2.219(1.0); 2.217(1.0); 2.213(1.2); 2.210(0.9); 2.204(1.3); 2.196(2.0);2.190(0.8); 2.183 (2.0); 2.174(1.4); 2.169(1.3); 2.162(1.3); 2.160(1.4);2.147(1.0); 2.112(1.1); 2.101(1.5); 2.100(1.5); 2.089(2.0); 2.077(2.0);2.066(1.9); 2.054(1.1); 2.043(0.8); 2.041(0.8); 2.030(0.6); 1.939(0.5);1.929(1.1); 1.918(0.6); 1.911(0.6); 1.901(1.2); 1.893 (1.0); 1.866(0.9);1.564(3.9); 0.008(0.7); 0.000(21.5); −0.009(0.6) Example 1516(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 7.262(50.0); 7.256(5.1); 7.222(1.7);7.214(1.9); 7.208(2.1); 7.200(1.9); 7.150(2.6); 7.142(3.0); 7.136(3.5);7.127(3.2); 7.100 (7.5); 7.085(0.5); 7.077(0.6); 7.071(2.2); 7.057(3.9);7.051(3.9); 7.047(1.7); 7.043(2.4); 7.037(5.9); 7.022(2.6); 4.259(3.2);4.250(3.3); 4.038(2.0); 4.027(2.1); 3.847(0.9); 3.839(1.9); 3.830(1.8);3.821(2.2); 3.813(1.0); 3.787(0.4); 3.758(0.6); 3.751 (0.7); 3.748(0.7);3.741(0.9); 3.730(1.3); 3.724(1.2); 3.719(0.6); 3.712(1.0); 3.706(0.6);3.700(0.7); 3.694(1.4); 3.685(1.7); 3.678(1.2); 3.669(1.7); 3.660(0.9);3.634(1.1); 3.627(1.2); 3.620(1.3); 3.616(1.2); 3.612(1.3); 3.609(1.1);3.602(1.0); 3.595 (0.9); 3.499(0.6); 3.492(0.9); 3.490(0.8); 3.483(1.0);3.476(1.0); 3.465(0.6); 3.458(0.5); 2.285(0.3); 2.279(0.3); 2.276(0.4);2.269(0.6); 2.262(0.6); 2.253(0.6); 2.246(0.7); 2.239(0.4); 2.236(0.4);2.230(0.4); 2.227(0.5); 2.218(0.7); 2.212(0.6); 2.209 (0.6); 2.203(1.3);2.195(1.4); 2.189(0.8); 2.186(0.7); 2.180(1.0); 2.171(0.6); 2.099(0.6);2.092(1.0); 2.084(1.2); 2.076(1.4); 2.068(13); 2.060(0.8); 2.052(0.7);2.044(0.4); 1.927(0.3); 1.920(0.6); 1.913(0.4); 1.908(0.4); 1.901(0.7);1.896(0.7); 1.890 (0.3); 1.885(0.3); 1.878(0.5); 1.541(6.6); 0.005(0.7);0.000(13.6); −0.006(0.5) Example 208(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 8.570(11.1); 8.567(11.4); 8.559(11.4); 8.555(11.2); 8.516(6.7);8.512(6.9); 8.505(6.9); 8.501(6.8); 7.718(14.0); 7.715(13.8);7.698(15.5); 7.694(17); 7.535(8.8); 7.531(8.5); 7.522(1.0); 7.515(9.8);7.511(9.4); 7.263(118.6); 7.219(15.9); 7.214(5.0); 7.207(18.3);7.199(16.3); 7.196(6.0); 7.190(6.5); 7.187(19.0); 7.181(8.5);7.180(8.7); 7.176(4.9); 7.169(4.8); 7.164(5.4); 7.160(7.3); 7.155(7.5);7.135(6.4); 7.110(12.6); 7.102(5.9); 7.098(13.8); 7.089(11.1);7.078(10.7); 7.071(1.9); 7.024(2.6); 7.003(4.9); 6.999(3.7); 6.995(3.1);6.989(3.4); 6.982(4.3); 6.977(6.2); 6.970(3.6); 6.968(3.3); 6.962(3.4);6.958(4.1); 6.949 (2.8); 6.944(3.1); 6.906(2.2); 6.903(2.5); 6.901(2.3);6.896(3.5); 6.893(2.6); 6.891(2.3); 6.887(2.3); 6.881(1.9); 6.875(2.3);6.871(1.7); 6.866(1.3); 4.363(8.6); 4.356(12.9); 4.337(11.1);4.333(16.0); 4.158(2.7); 4.141(8.1); 4.131(5.7); 4.123(3.5); 4.117(9.3); 4.107(8.1); 4.098(2.7); 4.094(3.9); 4.083(3.6); 3.625(1.9);3.611(3.9); 3.597(4.7); 3.583(5.5); 3.569(28.); 3.519(2.8); 3.505(5.6);3.491(6.7); 3.483(11.2); 3.478(9.2); 3.464(6.9); 3.455(2.4); 3.449(3.2);3.437(3.0); 3.421(2.2); 3.408(4.6); 3.394 (5.3); 3.388(5.5); 3.380(3.5);3.374(5.2); 3.367(3.4); 3.360(3.5); 3.347(3.1); 2.955(4.5); 2.880(3.8);2.878(3.7); 2.405(5.2); 2.390(7.5); 2.388(7.6); 2.374(6.6); 2.372(7.7);2.356(4.7); 2.103(2.0); 2.089(4.0); 2.079(2.2); 2.075(2.3); 2.068(3.3);2.065 (4.4); 2.055(5.6); 2.052(2.8); 2.045(3.0); 2.041(2.8); 2.031(5.3);2.017(2.5); 1.883(2.5); 1.872(2.8); 1.868(3.0); 1.863(3.0); 1.857(3.0);1.853(3.3); 1.848(4.5); 1.838(4.5); 1.834(2.5); 1.829(2.4); 1.823(2.2);1.818(2.3); 1.814(2.0); 1.803(1.8); 1.624 (2.7); 0.008(1.4);0.000(44.8); −0.009(1.2) Example 208 threo(Iba): ¹H-NMR (400.0 MHz.CDCl₃): δ = 8.574(1.9); 8.570(2.0); 8.563(2.0); 8.559(2.0); 8.519(10.6);8.515(11.0); 8.508(10.9); 8.504(10.9); 7.723(2.4); 7.720(2.4);7.703(2.6); 7.699(2.5); 7.538(13.3); 7.534(13.7); 7.517(15.0);7.513(14.7); 7.261(206.1); 7.223(2.7); 7.217(0.9); 7.211(3.7);7.202(3.2); 7.199(1.0); 7.191(3.4); 7.182(1.6); 7.178(1.0); 7.172(0.9);7.167(1.1); 7.162(1.4); 7.157(1.5); 7.138(1.2); 7.112 (16.2);7.100(15.5); 7.091(14.3); 7.080(14.1); 7.024(4.2); 7.003(7.8);7.000(5.1); 6.995(4.9); 6.989(5.3); 6.983(6.); 6.978 (9.3); 6.971(5.7);6.968(5.2); 6.962(5.5); 6.958(6.5); 6.950(4.2); 6.944(4.8); 6.909(3.6);6.905(3.9); 6.903(3.7); 6.899(5.6); 6.895(4.2); 6.893(3.7); 6.889(3.7);6.884(2.9); 6.877(3.7); 6.874(2.7); 6.868(2.1); 4.366(12.7); 4.360(2.8);4.341(16.0); 4.160 (4.3); 4.143(7.2); 4.134(4.0); 4.126(4.6);4.117(5.6); 4.109(1.8); 4.100(3.6); 4.085(0.7); 3.631(3.3); 3.617(6.8);3.603(8.4); 3.589(9.6); 3.575(4.9); 3.523(0.6); 3.509(1.1); 3.495(1.5);3.488(5.1); 3.481(2.1); 3.472(7.5); 3.461(3.9); 3.454(5.6); 3.443 (5.1);3.427(3.7); 3.412(1.0); 3.398(1.1); 3.392(1.1); 3.384(0.7); 3.378(1.1);3.371(0.7); 3.364(0.7); 3.351(0.6); 2.409(8.5); 2.393(12.7);2.377(12.6); 2.361(7.8); 2.093(0.7); 2.069(0.8); 2.058(1.5); 2.048(0.5);2.045(0.5); 2.034(0.9); 1.873(0.5); 1.868 (0.6); 1.864(0.6); 1.858(0.6);1.853(0.6); 1.849(0.8); 1.838(0.8); 1.607(3.5); 0.008(2.1); 0.000(77.2);−0.009(2.2) Example 1531(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =7.288(3.5); 7.262(50.0); 7.188(0.4); 7.174(1.0); 7.168(1.6); 7.155(3.2);7.139(3.2); 7.131(12.3); 7.125(1.8); 7.117 (0.8); 7.112(0.6);7.109(0.5); 7.104(0.5); 7.100(0.4); 7.085(0.3); 7.051(1.5); 7.047(1.6);7.039(1.7); 7.034(2.4); 7.029(1.6); 7.021(1.5); 7.017(1.4); 6.980(0.6);6.973(0.5); 6.966(0.6); 6.922(2.2); 6.915(1.7); 6.907(1.9); 4.268(5.1);4.260(5.2); 4.040 (1.4); 4.029(1.5); 3.857(1.4); 3.849(2.9); 3.840(2.7);3.831(3.3); 3.823(1.6); 3.772(0.4); 3.765(0.6); 3.763(0.5); 3.756(0.6);3.747(0.7); 3.745(0.7); 3.738(0.7); 3.731(0.5); 3.724(0.8); 3.718(0.5);3.710(1.6); 3.701(2.7); 3.694(1.9); 3.692(1.7); 3.685 (2.7); 3.676(1.4);3.642(1.7); 3.635(1.9); 3.628(2.1); 3.624(1.9); 3.621(2.1); 3.618(1.7);3.610(1.5); 3.603(1.4); 3.504(0.5); 3.497(0.6); 3.490(2.3); 3.481(0.8);3.470(0.4); 3.463(0.4); 2.252(0.4); 2.245(0.5); 2.236(0.5); 2.228(0.5);2.222(0.9); 2.214 (1.2); 2.208(0.9); 2.204(0.9); 2.199(1.9); 2.190(2.2);2.184(1.3); 2.181(1.2); 2.175(1.5); 2.166(0.9); 2.107(1.0); 2.100(1.6);2.092(1.9); 2.084(2.0); 2.076(1.9); 2.068(1.3); 2.061(1.0); 2.052(0.6);1.925(0.5); 1.907(0.6); 1.901(0.6); 1.883(0.4); 1.566 (5.3);0.000(14.6); −0.006(0.5) Example 1272(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 8.623(13.3); 8.620(13.8); 8.565(11.5); 8.561(11.5); 8.162(16.0);8.159(15.6); 7.926(13.9); 7.922(13.8); 7.519 (6.5); 7.383(2.4);7.369(2.7); 7.364(5.2); 7.349(5.1); 7.344(3.4); 7.329(3.5); 7.310(1.5);7.308(0.7); 7.291(1.3); 7.286(1.7); 7.277(2.8); 7.271(5.2); 7.270(5.8);7.269(7.2); 7.260(1202.0); 7.247(4.0); 7.231(2.5); 7.226(5.9);7.212(4.5); 7.206(3.8); 7.198(1.2); 7.192(2.8); 7.169(1.0); 7.081(8.0);7.078(6.4); 7.075(4.7); 7.060(7.4); 7.058(7.4); 7.054(6.3); 7.052(4.4);7.043 (4.2); 7.038(5.1); 7.033(4.7); 7.020(3.9); 7.016(4.1); 7.010(2.3);6.996(6.6); 6.969(2.1); 6.967(2.1); 6.963(2.2); 6.960(2.4); 6.948(3.4);6.946(3.8); 6.942(3.6); 6.939(4.2); 6.927(1.8); 6.925(1.9); 6.921(1.9);6.918(2.0); 6.888(5.0); 6.886(4.5); 6.881 (3.7); 6.876(4.2); 6.870(6.5);6.858(3.5); 6.852(3.5); 6.847(2.1); 4.302(8.8); 4.280(14.4); 4.254(8.3);3.725(2.1); 3.711(2.6); 3.698(3.0); 3.687(2.9); 3.684(3.0); 3.673(2.5);3.639(2.2); 3.626(4.1); 3.613(6.3); 3.599(5.5); 3.590(5.8); 3.586(5.1);3.581 (5.0); 3.566(3.9); 3.556(3.7); 3.348(2.6); 3.337(4.0); 3.326(4.5);3.321(2.9); 3.314(5.9); 3.310(4.4); 3.303(3.3); 3.299(4.3); 3.287 (4.6);3.276(2.4); 2.502(1.0); 2.493(1.2); 2.488(1.4); 2.479(2.1); 2.467(1.8);2.453(1.9); 2.444(2.7); 2.435(1.6); 2.429(1.4); 2.421(1.3); 2.276(1.5);2.265(3.0); 2.254(1.4); 2.249(1.5); 2.238(3.0); 2.230(2.5); 2.220(1.2);2.214(1.2); 2.203(2.1); 2.192 (1.0); 2.089(1.0); 2.078(2.0); 2.065(1.6);2.053(2.7); 2.043(4.0); 2.030(2.7); 2.017(3.6); 2.006(2.1); 1.977(1.8);1.964(2.6); 1.954(2.2); 1.952(2.4); 1.942(3.3); 1.929(3.0); 1.919(1.2);1.908(1.3); 1.894(0.9); 1.529(6.9); 1.255(1.0); 0.331(1.0); 0.238 (0.8);0.157(1.8); 0.146(1.2); 0.008(12.9); 0.000(468.1); −0.009(13.6);−0.150(1.4) Example 1781(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.749(7.1); 8.735(14.0); 7.600(7.8); 7.480(16.0); 7.301(2.8);7.296(2.9); 7.285(2.9); 7.279(3.0); 7.263(83.3); 7.224(5.4); 7.218(5.7);7.207(5.5); 7.201(5.6); 7.125(1.6); 7.104(5.9); 7.101(5.9); 7.083(7.3);7.079(14.8); 7.072(3.1); 7.067(2.7); 7.058 (8.6); 7.051(0.8);7.046(0.7); 7.007(3.7); 7.001(3.7); 6.996(4.1); 6.990(3.7); 6.986(2.6);6.980(2.4); 6.975(2.4); 6.969(2.1); 4.283(8.0); 4.269(8.4); 4.038(4.1);4.020(4.7); 3.839(2.3); 3.826(5.3); 3.813(5.2); 3.806(1.6); 3.799(7.5);3.787(4.7); 3.783 (4.5); 3.773(2.9); 3.769(3.2); 3.759(4.1); 3.753(1.6);3.744(2.8); 3.739(1.5); 3.727(1.7); 3.717(1.6); 3.712(1.6); 3.702(1.3);3.609(2.8); 3.598(3.2); 3.587(3.2); 3.582(2.7); 3.576(3.2); 3.571(2.7);3.560(2.5); 3.549(2.3); 3.486(3.4); 3.474(1.3); 3.463 (1.5); 3.449(1.8);3.438(1.6); 3.436(1.6); 3.423(1.2); 3.412(1.2); 2.958(3.8); 2.881(3.2);2.880(3.1); 2.347(0.6); 2.338(0.7); 2.333(0.7); 2.323(1.2); 2.313(1.2);2.309(0.8); 2.303(1.0); 2.298(1.2); 2.288(1.5); 2.278(1.0); 2.274(1.6);2.262(1.7); 2.253 (1.1); 2.248(1.2); 2.239(3.1); 2.226(3.6); 2.217(2.2);2.212(2.0); 2.204(2.6); 2.191(1.6); 2.158(1.7); 2.146(2.7); 2.135(3.2);2.123(3.5); 2.111(3.0); 2.099(1.8); 2.088(1.4); 2.076(0.9); 2.015(0.47);.005(1.3); 1.994(0.8); 1.987(0.8); 1.977(1.4); 1.970 (1.2); 1.959(0.6);1.952(0.7); 1.942(1.0); 1.932(0.6); 1.753(6.0); 0.008(1.1); 0.000(31.9);−0.009(0.9) Example 1700(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.005(1.8); 7.291(3.2); 7.285(3.4); 7.274(3.2); 7.269(3.7); 7.262(60.2);7.230(6.1); 7.224(6.4); 7.213(6.3); 7.207(6.3); 7.123 (1.7); 7.116(5.3);7.102(6.4); 7.094(14.3); 7.086(3.5); 7.081(7.6); 7.073(11.9);7.069(3.7); 7.065(1.2); 7.059(1.0); 7.053 (0.8); 7.044(4.5); 7.038(4.3);7.032(4.8); 7.027(4.4); 7.022(2.8); 7.016(2.5); 7.011(2.4); 7.005(2.2);6.998(0.5); 6.378(3.1); 6.377(3.1); 6.373(5.8); 6.372(5.8); 6.369(6.4);6.364(10.8); 6.355(6.5); 6.282(10.0); 6.278(10.1); 6.272(8.2);6.268(8.1); 6.261 (5.1); 6.256(5.1); 6.251(4.3); 6.247(4.2); 4.138(9.2);4.124(9.5); 3.950(5.1); 3.931(5.5); 3.819(2.4); 3.806(5.3); 3.792(5.1);3.779(7.2); 3.770(1.8); 3.766(3.6); 3.761(1.7); 3.756(1.6); 3.744(2.1);3.734(1.9); 3.729(1.9); 3.719(1.7); 3.653(3.3); 3.641 (3.7); 3.632(3.8);3.626(2.9); 3.620(3.8); 3.614(2.9); 3.605(2.8); 3.593(2.6); 3.562(1.7);3.550(1.9); 3.538(2.1); 3.535(1.7); 3.526(2.1); 3.523(1.8); 3.511(1.6);3.499(1.4); 3.485(6.8); 3.458(0.7); 3.450(1.0); 3.441(1.0); 3.433(2.1);3.429(2.2); 3.420 (3.2); 3.413(3.5); 3.404(3.2); 3.396(3.3); 3.390(2.6);3.381(1.3); 3.375(1.2); 2.958(16.0); 2.880(13.4); 2.879(12.9);2.281(0.7); 2.272(0.7); 2.267(0.8); 2.258(1.5); 2.247(1.2); 2.243(0.9);2.237(1.0); 2.232(1.2); 2.223(1.8); 2.214(0.9); 2.208(0.9); 2.199 (0.8);2.146(0.8); 42.133(1.7); 2.125(0.9); 2.120(1.1); 2.111(3.5); 2.098(4.8);2.090(2.8); 2.085(2.4); 2.077(4.2); 2.071(2.5); 2.063(2.5); 2.059(4.6);2.047(4.3); 2.035(4.6); 2.023(3.4); 2.012(1.7); 2.000(1.7); 1.988(0.8);1.952(0.9); 1.941(1.4); 1.930 (0.9); 1.923(0.9); 1.917(1.); 1.913(1.5);1.906(1.3); 1.902(1.0); 1.896(0.8); 1.888(0.8); 1.878(1.1); 1.867(0.7);1.489(10.1); 0.008(0.7); 0.000(22.5); −0.009(0.7) Example 1538(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 7.345(0.7); 7.341(0.7); 7.334(0.7);7.330(0.7); 7.300(2.5); 7.262(50.0); 7.253(2.3); 7.250(2.1); 7.154(0.6);7.142 (8.3); 7.130(2.0); 7.126(1.2); 7.116(4.3); 7.107(0.7); 7.102(2.8);7.093(0.3); 7.085(0.4); 7.045(1.3); 7.041(1.4); 7.038(1.5); 7.034(1.4);7.032(1.1); 7.027(1.0); 7.024(1.0); 7.020(0.8); 4.258(3.3); 4.249(3.4);4.039(1.1); 4.028(1.1); 3.858(0.9); 3.850 (1.9); 3.841(1.8); 3.832(2.2);3.824(1.1); 3.773(0.3); 3.766(0.4); 3.764(0.4); 3.755(0.5); 3.748(0.4);3.746(0.5); 3.740(0.5); 3.735(0.4); 3.730(0.3); 3.723(0.6); 3.716(0.4);3.711(0.4); 3.706(1.2); 3.697(1.8); 3.690(1.2); 3.687(1.1); 3.681(1.8);3.672 (0.9); 3.644(1.1); 3.638(1.2); 3.630(1.3); 3.627(1.2); 3.623(1.3);3.620(1.2); 3.612(1.0); 3.605(0.9); 3.505(0.4); 3.498(0.4); 3.491(2.3);3.481(0.5); 3.471(0.3); 2.243(0.3); 2.236(0.4); 2.227(0.4); 2.220(0.7);2.211(0.9); 2.206(0.6); 2.203(0.7); 2.197 (1.3); 2.188(1.4); 2.182(0.8);2.179(0.8); 2.173(1.0); 2.164(0.6); 2.103(0.6); 2.095(1.0); 2.088(1.2);2.080(1.4); 2.072(1.3); 2.064(0.8); 2.056(0.6); 2.049(0.4); 1.925(0.3);1.906(0.4); 1.901(0.4); 1.556(3.1); 0.005(0.7); 0.000(14.1); −0.006(0.5)Example 532 erythro(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.341(15.5);8.339(15.4); 8.328(16.0); 8.326(15.5); 8.308(0.8); 7.519(4.8);7.379(0.6); 7.310(1.0); 7.293(1.7); 7.260(903.9); 7.229(0.7);7.210(1.3); 7.163(5.1); 7.142(8.1); 7.138(6.3); 7.121(7.6); 7.116(20.9);7.112(19.5); 7.102(5.3); 7.097(10.7); 7.084(5.1); 7.078(5.8);7.070(5.1); 7.058(4.8); 7.052(4.9); 7.032(12.4); 7.028(11.3);7.018(11.4); 7.015(10.7); 6.996(5.2); 6.975(0.8); 6.918(3.2);6.913(4.0); 6.909(5.6); 6.904(4.3); 6.898(4.3); 6.892(3.7); 6.887(4.7);6.883(3.3); 6.877(2.4); 5.299 (4.5); 4.032(13.8); 4.014(14.6);3.709(2.1); 3.696(3.1); 3.683(4.1); 3.672(3.6); 3.658(2.6); 3.384(4.7);3.374(5.3); 3.366 (5.1); 3.356(10.5); 3.346(7.1); 3.338(5.6);3.328(5.2); 2.288(2.0); 2.278(2.2); 2.273(2.4); 2.263(4.3); 2.252(4.3);2.242(3.4); 2.238(4.3); 2.228(5.8); 2.218(3.2); 2.214(3.0); 2.204(2.6);2.170(0.6); 2.088(2.8); 2.077(5.2); 2.067(3.0); 2.061(2.7); 2.050 (5.2);2.042(4.5); 2.031(2.0); 2.025(2.2); 2.014(3.4); 2.004(1.9); 1.541(60.1);1.333(3.2); 1.284(6.3); 1.256(5.0); 0.880(0.8); 0.146(1.0); 0.008(9.2);0.000(342.5); −0.006(4.9); −0.009(11.0); −0.051(0.6); −0.150(1.1)(5.40.880(1.40.146(1.40.032(0.40.008(9.6); 0.000(325.4-0.009(9.2);−0.050(1.0); −0.150(0.9) Example 647(Iba): ¹H-NMR (600.1 MHz. CDCl₃): δ= 8.185(0.3); 8.181(0.3); 8.041(0.3); 8.031(0.4); 8.027(0.4);8.018(0.3); 7.449(0.3); 7.446(0.3); 7.438(0.3); 7.433 (0.4);7.261(50.0); 7.211(0.4); 7.197(0.7); 7.058(0.3); 7.054(0.3); 7.051(0.3);7.047(0.5); 7.037(0.4); 7.032(0.4); 7.025(0.7); 7.011(0.8); 6.842(0.4);6.833(0.4); 6.828(0.4); 6.819(0.3); 4.211(0.4); 4.194(0.4); 4.144(0.7);4.126(0.7); 3.758(0.4); 3.749 (0.4); 3.740(0.4); 1.557(3.5);0.000(13.9); −0.006(0.5) Example 1137(Iba): ¹H-NMR (600.1 MHz. CDCl₃): δ= 8.095(3.2); 8.086(8.3); 8.076(5.9); 7.303(1.9); 7.290(4.4);7.279(4.1); 7.277(4.2); 7.263(42.9); 7.024(1.7); 7.021 (1.8);7.010(4.0); 7.007(3.4); 6.996(3.2); 6.983(3.0); 6.970(2.1); 6.952(2.0);6.946(4.5); 6.933(4.6); 6.900(3.2); 6.884 (3.2); 6.700(2.4); 6.691(2.4);6.671(4.7); 6.663(4.6); 6.528(4.4); 6.487(8.6); 4.193(5.8); 4.181(5.9);4.027(0.4); 4.012(3.0); 4.000 (3.0); 3.908(50.0); 3.708(1.5);3.699(3.0); 3.690(3.2); 3.681(3.4); 3.672(1.7); 3.645(0.8); 3.638(1.0);3.635(1.0); 3.628(1.6); 3.620(1.1); 3.617(1.0); 3.610(0.9); 3.488(3.6);3.485(2.0); 3.476(2.0); 3.471(2.0); 3.467(1.8); 3.462(2.1); 3.458(1.8);3.453 (1.6); 3.445(1.5); 3.378(0.9); 3.370(1.0); 3.362(1.3); 3.354(1.2);3.345(0.9); 3.337(0.8); 3.298(1.9); 3.288(3.2); 3.282(3.3); 3.277(2.4);3.272(2.9); 3.262(1.9); 2.265(0.4); 2.259(0.5); 2.255(0.5); 2.249(0.8);2.242(0.9); 2.232(0.9); 2.226(1.0); 2.220 (0.6); 2.216(0.6); 2.210(0.5);2.107(0.8); 2.097(1.5); 2.095(1.4); 2.083(2.9); 2.074(4.4); 2.066(4.7);2.060(6.6); 2.050(6.6); 2.043(6.4); 2.034(4.8); 2.027(2.9); 2.019(2.3);2.011(1.4); 0.000(11.5) Example 1558(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 7.997(2.2); 7.266(38.5); 7.258(12.2); 7.199(1.5); 7.179(3.9);7.159(6.1); 7.136(6.6); 7.125(2.3); 7.115(4.9); 7.105(20.5); 7.093(1.9); 7.067(2.6); 7.061(2.8); 7.049(2.8); 7.042(3.8); 7.035(3.0);7.022(2.6); 7.017(2.7); 6.997(1.3); 6.992(1.7); 6.987(2.2); 6.983(1.9);6.977(1.8); 6.971(1.5); 6.966(1.8); 6.961(1.5); 6.939(2.9); 6.934(3.6);6.929(3.0); 6.923(2.8); 6.918(2.6); 6.913(3.0); 6.908(2.4); 4.283(7.9);4.269(8.2); 4.050(4.7); 4.033(5.2); 3.861(2.1); 3.849(4.3); 3.835(4.2);3.822(5.4); 3.809(2.7); 3.779(1.3); 3.769(1.6); 3.765(1.7); 3.752(2.0);3.742(2.0); 3.738(2.0); 3.728(1.6); 3.716(1.4); 3.707(1.6); 3.699(1.4);3.689 (2.8); 3.680(3.7); 3.666(4.8); 3.657(3.6); 3.652(5.4); 3.642(5.9);3.630(5.3); 3.625(3.3); 3.619(3.5); 3.614(2.8); 3.603(2.4); 3.592(2.2);3.517(1.5); 3.506(1.8); 3.491(2.6); 3.483(7.9); 3.466(1.5); 3.455(1.4);2.961(16.0); 2.878(13.9); 2.280(0.7); 2.270 (0.8); 2.266(0.9);2.256(1.3); 2.245(1.6); 2.232(2.5); 2.220(2.5); 2.210(2.1); 2.205(1.9);2.196(3.5); 2.183(3.2); 2.174(2.2); 2.169(2.1); 2.160(2.4); 2.148(1.5);2.113(1.7); 2.101(2.5); 2.090(3.1); 2.078(3.3); 2.067(2.9); 2.055(1.7);2.043(1.4); 2.031 (0.9); 1.937(0.9); 1.927(1.6); 1.917(1.0); 1.910(0.9);1.900(1.9); 1.892(1.); 1.882(0.8); 1.875(0.8); 1.864(1.4); 1.854(0.7)1.706(4.1); 0.008(0.7); 0.000(14.6); −0.008(0.6) Example 1295(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.623(14.4); 8.620(15.2); 8.570(12.8);8.566(13.8); 8.199(15.6); 8.196(16.0); 7.971(13.3); 7.968(14.3); 7.519(4.0); 7.385(7.9); 7.367(6.7); 7.260(668.8); 7.237(14.3); 7.231(13.7);7.220(11.5); 7.214(10.7); 7.171(18.4); 7.168(19.9); 7.157(11.6);7.153(17.4); 7.038(5.1); 7.017(11.7); 6.996(12.9); 6.981(5.7);6.976(6.1); 6.970(6.5); 6.965(6.1); 4.281(15.1); 4.260(12.8);4.256(11.9); 3.733(2.4); 3.721(4.4); 3.706(4.1); 3.693(4.5); 3.681(3.3);3.645(3.3); 3.632(5.5); 3.619(5.8); 3.605 (8.3); 3.593(7.4); 3.579(7.2);3.569(8.6); 3.556(6.1); 3.545(5.8); 3.533(3.5); 3.346(3.1); 3.335(4.2);3.320(6.5); 3.307(6.8); 3.297(6.7); 3.285(4.0); 3.280(3.4); 3.269(2.7);2.464(2.3); 2.452(2.9); 2.442(2.9); 2.430(2.8); 2.420(2.0); 2.229(3.2);2.202 (3.7); 2.194(3.2); 2.167(2.6); 2.058(1.4); 2.047(2.2); 2.035(2.1);2.023(3.6); 2.012(4.8); 1.999(3.6); 1.987(4.2); 1.952(2.1); 1.940(3.6);1.930(3.5); 1.918(4.4); 1.905(3.8); 1.883(2.0); 1.509(8.9); 0.146(1.3);0.000(252.0); −0.150(1.8) Example 289 erythro1(Iba): ¹H-NMR (400.0 MHz.CDCl₃): δ = 8.401(3.2); 8.395(3.4); 7.975(2.5); 7.380(0.9); 7.375(1.1);7.369(0.8); 7.358(1.0); 7.352(1.2); 7.347(0.8); 7.269(0.5); 7.268 (0.6);7.267(0.7); 7.261(42.5); 7.170(0.8); 7.149(1.4); 7.146(0.9); 7.129(1.1);7.125(1.3); 7.104(0.8); 7.037(0.7); 7.031(0.7); 7.019(0.7); 7.012(0.9);7.005(0.7); 6.993(0.6); 6.987(0.7); 6.890(0.5); 6.887(0.7); 6.881(0.9);6.877(0.7); 6.871(0.6); 6.865 (0.6); 6.860(0.7); 6.856(0.5);5.299(16.0); 4.487(2.1); 4.472(2.1); 3.633(0.9); 3.616(0.9); 3.092(0.9);3.072(0.9); 3.049(1.4); 3.029(1.3); 2.907(1.4); 2.891(1.4); 2.864(1.0);2.848(0.9); 0.000(15.4) Example 107(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.492(0.7); 8.489(1.4); 8.485(0.8); 8.481(0.8); 8.477(1.4); 8.474(0.8);8.419(0.7); 8.416(1.3); 8.412(0.8); 8.408(0.8); 8.405 (1.38.401(0.7);7.434(0.8); 7.430(0.8); 7.416(1.4); 7.413(1.4); 7.410(2.6); 7.407(1.1);7.399(1.3); 7.393(1.4); 7.390(1.2); 7.386(1.1); 7.295(1.3); 7.2843(1.6);7.2835(1.5); 7.273(1.7); 7.271(0.5); 7.270(0.5); 7.269(0.5); 7.268(0.6);7.2674(0.7); 7.2666 (0.8); 7.266(1.0); 7.261(77.3); 7.2543(1.0);7.2536(1.0); 7.252(1.2); 7.248(0.6); 7.243(0.8); 7.241(0.8); 7.237(1.2);7.233 (1.0); 7.227(0.9); 7.221(1.1); 7.220(1.5); 7.216(2.1); 7.197(1.3);7.193(1.2); 7.177(1.4); 7.172(2.5); 7.166(3.3); 7.155(2.4); 7.151(3.2);7.145(1.2); 7.134(0.7); 7.130(1.2); 7.009(1.0); 7.004(1.0); 6.997(1.2);6.992(1.0); 6.986(1.8); 6.965(2.4); 6.944 (0.8); 4.345(1.8); 4.337(1.7);4.321(2.0); 4.311(1.9); 4.148(1.1); 4.130(3.3); 4.112(3.4); 4.094(1.1);3.906(0.7); 3.896(0.6); 3.892(0.8); 3.889(0.6); 3.881(0.8); 3.661(0.8);3.648(1.0); 3.634(1.0); 3.620(0.6); 3.535(0.7); 3.522(1.0); 3.508(1.1);3.500(0.6); 3.494(0.7); 3.486(0.5); 3.480(0.6); 3.466(0.7); 3.410(0.6);3.397(0.7); 3.390(0.7); 3.377(0.7); 2.410(0.9); 2.406(0.6); 2.401 (0.6);2.396(1.0); 2.387(0.9); 2.374(0.9); 2.043(16.0); 2.036(0.5); 2.024(0.5);1.841(0.5); 1.830(0.5); 1.625(0.8); 1.286(0.7); 1.284(0.7); 1.276(4.9);1.258(10.4); 1.241(4.8); 0.008(0.8); 0.000(27.6); −0.009(0.8) Example597(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.373(13.1); 8.185(16.0);7.421(0.7); 7.419(0.7); 7.406(1.0); 7.402(1.7); 7.400(1.4); 7.388(1.5);7.384(1.6); 7.381(1.2); 7.370 (0.7); 7.366(1.0); 7.293(0.6);7.261(45.8); 7.239(1.0); 7.224(1.7); 7.219(1.4); 7.215(1.6); 7.211(0.9);7.205(1.47.202(1.7); 7.198(1.6); 7.194(1.0); 7.183(1.7); 7.174(1.8);7.171(2.9); 7.168(2.0); 7.151(2.1); 7.117(3.6); 7.114(3.5); 7.095(4.4);7.092 (4.2); 7.076(1.2); 7.074(1.2); 7.070(0.7); 6.997(0.5); 6.969(3.1);6.954(4.2); 6.949(5.1); 6.941(2.5); 6.936(3.2); 6.933(3.4); 6.928(2.4);6.923(1.5); 6.920(1.7); 6.914(0.7); 5.298(2.5); 4.274(3.2); 4.249(3.7);4.205(3.6); 4.178(4.6); 3.996(1.0); 3.987 (1.0); 3.968(1.7); 3.959(1.7);3.941(0.8); 3.931(0.8); 3.909(0.8); 3.897(0.8); 3.883(1.3); 3.871(1.3);3.857(0.7); 3.845(0.7); 3.768(1.1); 3.755(1.8); 3.741(2.2); 3.728(2.0);3.715(1.3); 3.607(0.9); 3.594(1.5); 3.581(2.0); 3.567(1.8); 3.554(1.1);3.480 (1.2); 3.468(1.4); 3.457(1.5); 3.453(1.3); 3.446(1.5); 3.441(1.3);3.430(1.2); 3.419(1.1); 3.395(1.0); 3.383(1.1); 3.372(1.2); 3.368(1.0);3.360(1.2); 3.356(1.0); 3.346(0.9); 3.334(0.8); 2.955(2.8); 2.879(2.4);2.564(0.6); 2.554(0.7); 2.550(0.7); 2.541 (1.0); 2.529(1.2); 2.518(1.2);2.506(1.3); 2.497(0.8); 2.493(0.7); 2.483(0.7); 2.317(0.5); 2.306(1.0);2.293(0.7); 2.290(0.7); 2.286(0.6); 2.278(1.1); 2.274(1.0); 2.271(1.0);2.267(0.8); 2.259(0.6); 2.255(0.5); 2.243(0.7); 2.073(0.6); 2.061(0.5);2.050 (0.8); 2.047(0.8); 2.042(0.7); 2.038(1.0); 2.035(0.8); 2.024(0.7);2.012(0.8); 1.932(0.6); 1.919(0.9); 1.906(0.8); 1.897(1.2); 1.884(1.1);1.874(0.5); 1.862(0.6); 1.516(1.5); 0.008(0.8); 0.000(18.0); −0.009(0.7)Example 491(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.608(13.1);8.526(7.1); 8.514(16.0); 8.501(13.0); 8.495(15.1); 7.521(1.3);7.422(11.2); 7.410(11.2); 7.397(11.9); 7.396 (12.0); 7.392(8.0);7.351(6.5); 7.345(5.1); 7.340(7.1); 7.331(16.3); 7.328(18.1);7.325(11.9); 7.321(10.0); 7.314(14.3); 7.306 (4.9); 7.303(5.8);7.301(5.7); 7.299(5.6); 7.295(4.8); 7.286(8.0); 7.283(9.7); 7.281(10.0);7.278(9.6); 7.271(8.9); 7.262 (219.4); 7.249(3.3); 7.231(6.7);7.212(10.2); 7.192(5.0); 7.154(8.4); 6.998(3.2); 6.990(4.3); 6.972(3.7);5.298(3.5); 4.333(6.1); 4.317(7.1); 4.157(7.3); 4.142(8.4); 4.044(2.1);3.944(2.3); 3.934(2.7); 3.916(2.9); 3.906(2.8); 3.892(2.1); 3.717(1.8);3.703 (3.5); 3.690(4.1); 3.676(4.5); 3.663(2.3); 3.613(2.8); 3.602(3.2);3.597(3.4); 3.586(6.4); 3.575(4.1); 3.570(4.1); 3.559 (3.5); 3.514(1.8);3.486(2.6); 3.455(1.4); 3.380(3.7); 3.367(4.1); 3.358(4.5); 3.353(3.5);3.345(4.3); 3.340(3.6); 3.331(3.5); 3.318 (3.2); 2.285(1.1); 2.273(1.8);2.260(1.4); 2.250(2.2); 2.245(2.2); 2.238(3.1); 2.225(2.4); 2.222(2.6);2.209(3.5); 2.197(2.6); 2.168(2.3); 2.153(3.2); 2.144(3.2); 2.137(3.0);2.130(3.2); 2.120(3.9); 2.106(5.4); 2.095(4.5); 2.084(4.8); 2.071(4.0);2.060 (1.8); 2.048(1.8); 2.035(1.0); 1.605(1.9); 1.255(0.7); 0.008(2.4);0.000(79.2); −0.009(2.3) Example 511(Ibs): ¹H-NMR (400.0 MHz. CDCl₃): δ= 8.609(12.9); 8.530(15.0); 8.517(15.4); 8.502(14.8); 7.598(4.4);7.592(4.6); 7.582(4.5); 7.577(4.5); 7.521(1.1); 7.435 (8.8); 7.422(8.7);7.348(3.6); 7.331(6.6); 7.318(4.1); 7.302(2.3); 7.296(2.3); 7.291(2.5);7.285(2.4); 7.281(3.1); 7.274(3.2); 7.269(3.9); 7.262(187.8);7.254(0.9); 7.2533(0.7); 7.2525(0.6); 7.252(0.5); 7.141(5.9);7.120(8.7); 7.100(4.6); 7.046(1.3); 7.025(6.5); 7.006(7.9); 6.998(3.6);5.299(16.0); 4.354(4.8); 4.338(5.6); 4.140(3.9); 4.124(4.5); 4.030(1.5);3.927(1.4); 3.918 (1.7); 3.913(1.5); 3.900(2.0); 3.889(1.7); 3.884(1.6);3.874(1.3); 3.740(1.3); 3.727(2.6); 3.714(2.9); 3.700(3.3); 3.688(1.9);3.632(1.8); 3.620(2.2); 3.616(2.3); 3.605(4.1); 3.594(2.6); 3.589(2.8);3.578(2.3); 3.497(1.9); 3.387(2.4); 3.374(2.7); 3.365 (3.0); 3.360(2.4);3.352(2.9); 3.347(2.5); 3.338(2.3); 3.325(2.1); 2.278(0.7); 2.266(1.2);2.250(0.9); 2.242(1.6); 2.238(1.6); 2.231(2.3); 2.215(2.0); 2.203(2.7);2.191(2.1); 2.161(2.2); 2.151(2.1); 2.146(2.0); 2.137(2.2); 2.125(2.8);2.113(3.9); 2.101 (3.2); 2.090(3.6); 2.078(2.9); 2.067(1.4); 2.054(1.4);2.042(0.41.600(0.9); 0.008(2.1); 0.000(69.7); -0.009(2.1) Example599(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.379(14.7); 8.197(16.0);7.519(0.8); 7.392(0.8); 7.387(1.2); 7.375(14.4); 7.370(10.1);7.358(5.7); 7.352(1.3); 7.341(1.0); 7.336(1.7); 7.295(0.5); 7.280(2.3);7.275(3.5); 7.270(2.3); 7.269(2.3); 7.267(1.9); 7.260(141.7);7.254(2.3); 7.236(1.1); 7.233 (1.6); 7.231(1.9); 7.228(2.2); 7.212(9.1);7.209(9.1); 7.193(3.1); 7.190(2.0); 7.174(4.3); 7.172(3.5); 7.156(1.7);7.153 (1.8); 7.075(1.9); 7.071(2.9); 7.056(1.4); 7.053(2.3); 6.996(0.9);4.249(3.8); 4.224(4.4); 4.180(3.9); 4.152(5.1); 3.989(0.9); 3.979(0.9);3.961(1.6); 3.952(1.5); 3.934(0.8); 3.924(0.7); 3.898(0.8); 3.886(0.8);3.872(1.4); 3.860(1.4); 3.845(0.7); 3.834. (0.7); 3.773(1.0);3.760(1.6); 3.746(2.0); 3.733(1.9); 3.720(1.2); 3.610(0.9); 3.597(1.5);3.583(2.1); 3.570(1.8); 3.557(1.2); 3.481(1.1); 3.470(1.2); 3.458(1.3);3.454(1.2); 3.447(1.3); 3.442(1.2); 3.431(1.1); 3.420(1.0); 3.396(1.1);3.384(1.1); 3.374 (1.4); 3.369(1.0); 3.362(1.2); 3.357(1.0); 3.347(0.9);3.335(0.9); 2.560(0.5); 2.550(0.6); 2.546(0.6); 2.537(1.0); 2.525(1.1);2.514 (1.1); 2.502(1.3); 2.492(0.8); 2.489(0.8); 2.479(0.7); 2.308(0.9);2.296(0.6); 2.292(0.7); 2.284(0.8); 2.280(1.0); 2.277 (0.9); 2.273(0.9);2.269(0.8); 2.261(0.5); 2.257(0.5); 2.245(0.7); 2.068(0.6); 2.045(0.8);2.041(0.9); 2.037(0.8); 2.033(1.1); 2.029 (0.9); 2.018(0.7); 2.006(0.9);1.922(0.7); 1.908(0.9); 1.896(0.8); 1.887(1.3); 1.873(1.2); 1.864(0.6);1.852(0.6); 0.008 (1.6); 0.000(53.0); −0.009(1.6) Example 100(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.503(1.6); 8.500(2.5); 8.497(1.6);8.491(1.7); 8.488(2.5); 8.418(2.2); 8.414(1.4); 8.409(1.4); 8.406(2.2);7.519(0.9); 7.469 (1.1); 7.465(1.2); 7.447(1.8); 7.445(2.4); 7.424(1.5);7.421(1.5); 7.325(1.6); 7.313(2.5); 7.303(2.3); 7.292(1.9); 7.282(1.7);7.260(161.3); 7.242(2.3); 7.239(2.3); 7.224(1.4); 7.219(2.8);7.216(3.0); 7.206(1.4); 7.198(3.4); 7.191(2.6); 7.187(3.3); 7.176 (3.5);7.166(1.9); 7.155(0.9); 7.150(1.5); 7.115(1.1); 7.110(1.4);7.095(0.47.089(0.9); 7.025(0.9); 7.004(1.47.001(1.2); 6.996(1.1);6.984(1.5); 6.980(2.5); 6.974(1.1); 6.959(1.6); 6.956(1.3); 6.947(1.1);6.934(0.9); 6.929(1.0); 6.881(0.9); 6.876 (1.2); 6.871(1.0); 6.865(0.9);6.854(0.9); 4.351(3.0); 4.337(2.6); 4.326(3.3); 4.311(2.9); 4.150(1.2);4.132(3.5); 4.115(3.5); 4.097(1.2); 3.950(0.6); 3.939(0.6); 3.928(1.4);3.918(1.4); 3.904(1.6); 3.893(1.5); 3.880(0.7); 3.871(0.6); 3.696(0.7);3.682(1.3); 3.668(1.5); 3.654(1.8); 3.641(1.0); 3.557(0.8); 3.543(1.5);3.529(2.1); 3.515(2.7); 3.501(1.7); 3.491(0.7); 3.485(0.8); 3.472 (0.7);3.423(1.1); 3.410(1.2); 3.402(1.3); 3.395(0.9); 3.389(1.2); 3.382(0.9);3.375(0.9); 3.362(0.8); 2.427(0.8); 2.417(1.5); 2.403(1.9); 2.394(1.8);2.381(1.9); 2.368(0.8); 2.233(7.8); 2.107(1.2); 2.091(0.8); 2.079(0.8);2.067(1.0); 2.056(1.3); 2.046 (16.0); 2.032(1.1); 2.019(0.5);1.882(0.6); 1.867(0.7); 1.862(0.7); 1.857(0.7); 1.847(1.0); 1.837(1.0);1.827(0.6); 1.277(4.2); 1.260(8.4); 1.242(4.1); 0.069(5.8); 0.008(2.6);0.000(57.3); −0.009(2.1) Example 289 erythro1(Iba): ¹H-NMR (400.0 MHz.CDCl₃): δ = 8.393(7.4); 8.195(7.2); 7.521(1.0); 7.295(0.6);7.262(185.3); 7.246(6.1); 7.155(4.0); 7.134(7.9); 7.131(5.5);7.114(6.1); 7.110 (7.9); 7.090(5.1); 7.083(4.2); 7.078(4.3); 7.065(4.4);7.059(5.5); 7.051(4.4); 7.039(4.0); 7.033(4.0); 6.998(1.1); 6.918 (4.2);6.914(5.2); 6.909(4.4); 6.903(3.9); 6.897(3.7); 6.892(4.3); 6.888(3.4);5.299(16.0); 4.046(10.1); 4.028(10.6); 3.708(2.7); 3.697(3.8);3.694(3.8); 3.682(5.1); 3.671(4.4); 3.667(4.2); 3.657(3.2); 3.483(2.2);3.474(2.6); 3.466(2.7); 3.456(4.3); 3.447 (2.9); 3.439(2.6); 3.429(2.1);3.391(3.0); 3.380(3.4); 3.367(4.6); 3.356(4.6); 3.341(2.9); 3.330(2.7);2.324(1.3); 2.310(1.7); 2.300(2.6); 2.289(3.2); 2.276(3.3); 2.265(3.4);2.255(2.2); 2.241(1.5); 2.096(1.7); 2.086(3.2); 2.075(2.1); 2.069(2.1);2.058 (3.9); 2.050(3.4); 2.040(1.6); 2.033(1.6); 2.023(2.3); 2.012(1.2);1.622(3.8); 1.333(0.8); 1.284(1.1); 1.256(1.6); 0.008(2.0); 0.000(64.2);−0.006(0.6); −0.007(0.5); −0.009(1.8) Example 620(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.381(16.0); 8.369(1.1); 8.243(1.1); 8.214(15.4);7.519(5.4); 7.293(0.6); 7.289(0.8); 7.260(956.7); 7.250(5.0); 7.244(2.3); 7.229(3.0); 7.226(3.7); 7.218(2.0); 7.209(3.2); 7.205(3.4);7.200(1.8); 7.185(2.0); 7.147(0.6); 7.128(1.3); 7.122(1.8); 7.118(1.4);7.112(1.2); 7.101(1.3); 7.093(1.8); 7.087(1.4); 7.071(2.0); 7.061(1.4);7.050(3.1); 7.043(1.5); 7.030(1.9); 7.026 (2.2); 7.006(1.7); 6.996(5.4);6.921(1.6); 5.299(2.1); 4.265(3.9); 4.240(4.4); 4.184(3.4); 4.157(4.4);3.974(0.8); 3.965(0.8); 3.946(1.4); 3.936(1.4); 3.917(0.7); 3.908(0.6);3.887(0.8); 3.875(0.8); 3.861(1.4); 3.848(1.4); 3.836(0.9); 3.823(0.7);3.779 (0.9); 3.766(1.4); 3.753(1.8); 3.740(1.7); 3.726(1.1); 3.636(1.0);3.623(1.6); 3.610(2.0); 3.597(1.9); 3.583(1.2); 3.478(0.9); 3.467(1.1);3.456(1.1); 3.444(1.2); 3.428(1.0); 3.411(1.0); 3.399(1.1); 3.388(1.2);3.377(1.2); 3.362(0.9); 3.350(0.9); 2.544 (0.6); 2.535(0.9); 2.522(1.0);2.510(1.0); 2.499(1.3); 2.490(0.7); 2.476(0.6); 2.294(0.8); 2.266(0.9);2.231(0.7); 2.040(1.1); 2.013(0.9); 2.005(0.7); 1.936(0.7); 1.923(1.0);1.912(0.9); 1.901(1.4); 1.888(1.2); 1.878(0.7); 1.865(0.7); 1.543(11.9);1.371 (0.9); 1.333(1.7); 1.284(2.4); 1.256(2.2); 0.146(1.0); 0.008(9.1);0.000(336.9); −0.009(9.9); −0.150(1.0) Example 84(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.385(4.0); 8.377(5.5); 8.374(7.4); 8.368(6.9);8.201(3.7); 7.959(69); 47.351(2.4); 7.345(3.2); 7.340(2.5); 7.328(3.5);7.322 (3.5); 7.316(2.8); 7.307(3.5); 7.291(4.2); 7.286(4.9); 7.278(2.6);7.272(6.6); 7.262(66.2); 7.251(4.4); 7.244(1.5); 7.041(1.1); 7.034(1.4);7.029(1.9); 7.022(3.0); 7.013(2.3); 7.010(3.1); 7.008(3.1); 7.003(3.4);7.001(3.5); 6.995(1.3); 6.989(1.6); 6.987 (1.6); 6.982(1.7); 6.966(2.4);6.956(1.5); 6.950(3.1); 6.947(3.6); 6.932(1.6); 6.927(1.8); 6.922(1.0);6.887(4.0); 6.868(3.8); 6.858(2.8); 6.853(3.1); 6.848(1.8); 6.835(2.4);6.830(3.0); 6.825(1.8); 5.299(16.0); 4.307(5.9); 4.292(6.1); 4.057(3.2);4.040 (3.4); 3.835(1.2); 3.798(1.6); 3.785(3.4); 3.772(3.5); 3.758(4.1);3.745(2.0); 3.690(0.9); 3.679(1.1); 3.675(1.1); 3.664 (1.6); 3.653(1.3);3.648(1.2); 3.638(1.0); 3.547(1.9); 3.535(2.2); 3.526(2.3); 3.520(2.0);3.514(2.4); 3.509(2.1); 3.499(2.4); 3.487 (2.3); 3.474(2.4); 3.460(2.7);3.446(2.0); 3.437(2.3); 3.422(1.1); 3.385(1.0); 3.373(1.2); 3.361(1.4);3.349(1.4); 3.346 (1.2); 3.335(1.0); 3.323(0.9); 2.320(0.5); 2.315(0.5);2.305(0.9); 2.295(1.0); 2.284(0.9); 2.280(1.0); 2.270(1.2); 2.259(1.1);2.245 (1.5); 2.237(0.8); 2.231(0.9); 2.223(2.2); 2.209(2.6); 2.202(1.6);2.195(1.5); 2.188(2.0); 2.174(1.3); 2.170(1.1); 2.162(1.3); 2.150(2.3);2.138(2.2); 2.127(2.8); 2.114(2.5); 2.102(1.8); 2.091(1.6); 2.084(0.8);2.078(1.0); 2.073(1.2); 2.065(1.0); 2.054 (0.6); 2.048(0.6); 2.043(0.8);2.038(0.8); 2.005(0.9); 1.752(1.5); 1.371(0.6); 1.286(0.9); 1.258(1.4);0.008(1.0); 0.000 (25.2); −0.009(1.2) Example 295(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.492(0.8); 8.488(1.6); 8.485(0.9); 8.480(0.9);8.477(1.6); 8.473(0.9); 8.421(0.8); 8.417(1.5); 8.414(0.9); 8.410(0.8);8.406 (1.5); 8.403(0.8); 7.557(1.4); 7.551(1.5); 7.541(1.4); 7.535(1.5);7.431(0.9); 7.428(0.9); 7.410(1.3); 7.407(1.5); 7.404(1.0); 7.387(1.2);7.383(1.1); 7.308(1.4); 7.302(1.5); 7.299(0.9); 7.293(3.2); 7.287(1.8);7.282(2.5); 7.278(1.2); 7.272(2.5); 7.266 (1.7); 7.261(74.3);7.250(1.0); 7.239(0.7); 7.236(0.8); 7.218(1.4); 7.216(0.9); 7.215(1.4);7.213(0.9); 7.195(1.4); 7.192(1.3); 7.177(1.4); 7.166(2.4); 7.155(1.6);7.148(2.0); 7.145(1.3); 7.134(0.7); 7.127(2.8); 7.107(1.5); 7.079(0.6);7.073(0.6); 7.067 (0.7); 7.062(0.6); 7.057(0.9); 7.051(0.9); 7.046(0.9);7.040(0.8); 6.965(1.9); 6.944(2.7); 6.923(1.3); 4.342(2.0); 4.332(1.8);4.318(2.2); 4.306(2.0); 4.148(1.1); 4.130(3.3); 4.112(3.3); 4.094(1.1);3.903(0.9); 3.892(0.7); 3.889(0.9); 3.878(0.9); 3.662(0.9); 3.648(1.0);3.634(1.0); 3.621(07); 43.535(0.8); 3.522(1.1); 3.508(1.2); 3.501(0.7);3.494(0.7); 3.486(0.6); 3.481(0.7); 3.467 (0.7); 3.453(0.5); 3.411(0.6);3.398(0.7); 3.390(0.7); 3.383(0.5); 3.377(0.7); 2.419(0.5); 2.409(0.8);2.405(0.6); 2.396(1.0); 2.387(1.1); 2.374(1.2); 2.095(0.9); 2.057(0.5);2.043(16.0); 2.035(0.6); 2.023(0.6); 1.842(0.6); 1.831(0.6); 1.588(0.7);1.333 (0.7); 1.284(1.1); 1.276(4.9); 1.258(10.4); 1.240(4.8);0.008(0.8); 0.000(27.5); −0.009(0.7) Example 619(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.384(14.1); 8.219(16.0); 7.588(2.5); 7.582(2.7);7.572(2.6); 7.566(2.7); 7.519(1.1); 7.431(2.4); 7.425(2.6); 7.415(2.5);7.410 (2.6); 7.325(1.3); 7.319(1.3); 7.314(1.5); 7.308(1.4); 7.304(1.9);7.298(1.9); 7.293(2.0); 7.287(1.7); 7.260(176.1); 7.191 (3.4);7.170(4.9); 7.150(2.8); 7.122(1.3); 7.116(1.2); 7.111(1.3); 7.105(1.3);7.101(1.7); 7.095(1.7); 7.089(1.7); 7.084(1.6); 7.010(3.9); 6.996(1.3);6.990(5.2); 6.969(2.6); 4.258(3.5); 4.233(4.0); 4.176(3.8); 4.148(4.9);3.972(0.9); 3.962(0.9); 3.944 (1.5); 3.935(1.5); 3.917(0.7); 3.907(0.7);3.879(0.8); 3.867(0.8); 3.853(1.4); 3.841(1.4); 3.828(0.8); 3.816(0.7);3.780(1.1); 3.767(1.7); 3.753(2.0); 3.740(2.0); 3.727(1.3); 3.632(1.0);3.619(1.6); 3.606(2.1); 3.593(2.0); 3.580(1.3); 3.477(1.2); 3.466(1.3);3.454(1.4); 3.450(1.3); 3.443(1.4); 3.439(1.3); 3.427(1.2); 3.415(1.1);3.409(1.2); 3.397(1.2); 3.386(1.3); 3.382(1.1); 3.375 (1.3); 3.371(1.1);3.360(1.0); 3.348(1.0); 2.553(0.6); 2.543(0.6); 2.539(0.6); 2.530(1.0);2.518(1.1); 2.507(1.1); 2.495(1.2); 2.485(0.8); 2.482(0.8); 2.472(0.6);2.297(0.9); 2.282(0.6); 2.270(1.0); 2.266(0.9); 2.262(0.9); 2.258(0.8);2.234(0.7); 2.071 (0.7); 2.059(0.5); 2.047(0.8); 2.044(0.9); 2.036(1.1);2.021(0.8); 2.009(0.9); 1.997(0.5); 1.928(0.7); 1.915(1.0); 1.904(0.9);1.893(1.3); 1.880(1.2); 1.870(0.7); 1.858(0.7); 1.845(0.5); 1.672(0.8);1.621(0.6); 0.008(2.0); 0.000(66.8); −0.009(2.0) Example 489(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.597(1.1); 8.576(1.6); 8.561(1.5);8.526(1.7); 8.494(2.3); 8.485(2.3); 8.469(1.4); 8.444(4.3); 8.371(2.7);8.358(2.7); 8.305 (4.3); 8.255(0.6); 7.844(2.4); 7.831(2.4); 7.714(2.8);7.701(2.7); 7.519(1.6); 7.311(2.9); 7.286(4.4); 7.260(284.4); 7.211(2.8); 7.191(1.7); 7.054(1.7); 7.042(1.8); 7.015(1.5); 6.996(2.3);6.961(1.6); 6.941(1.4); 6.878(1.7); 6.826(0.9); 6.805(1.2); 6.700(0.6);5.298(1.2); 4.469(0.7); 4.444(1.3); 4.429(1.2); 4.419(1.1); 4.404(0.8);4.380(0.6); 4.365(0.8); 4.348(0.7); 4.335 (0.7); 4.254(1.1); 4.084(1.0);4.063(1.0); 3.947(0.6); 3.795(0.9); 3.782(0.7); 3.690(0.9); 3.609(0.9);3.540(1.5); 3.531(1.6); 3.513 (1.6); 3.495(2.2); 3.471(16.0);3.440(1.7); 3.105(0.6); 3.082(0.6); 2.924(0.5); 2.473(2.5); 2.457(2.3);2.449(2.4); 2.423 (1.2); 2.186(1.7); 2.163(1.7); 1.253(0.9); 0.007(4.2);0.000(100.3); −0.001(97.6); −0.008(5.1); −0.150(0.5) Example 511(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.620(14.0); 8.556(12.5); 8.543(12.3);8.521(13.4); 7.920(7.6); 7.906(8.6); 7.898(8.8); 7.884(7.8); 7.843(1.2);7.836(9.9); 7.831(3.8); 7.823(10.5); 7.819(5.1); 7.817(5.0);7.814(11.0); 7.806(3.8); 7.800(10.4); 7.793(1.1); 7.603(5.1);7.597(5.3); 7.588(5.2); 7.582(5.1); 7.525(5.9); 7.519(4.6); 7.512(5.8);7.495(4.0); 7.483(3.7); 7.342(3.4); 7.309(3.1); 7.303(3.0); 7.298 (3.2);7.292(3.4); 7.288(3.9); 7.282(4.0); 7.277(4.2); 7.270(4.7);7.260(243.0); 7.151(6.7); 7.130(10.9); 7.127(16.0); 7.121 (5.0);7.110(11.4); 7.104(25.6); 7.098(5.6); 7.089(6.2); 7.083(22.9);7.077(5.3); 7.065(3.9); 7.060(11.9); 7.037(6.2); 7.017 (5.3);6.996(4.1); 5.298(10.2); 4.412(1.9); 4.401(2.1); 4.386(2.2); 4.300(3.2);4.286(3.6); 4.275(3.1); 4.260(4.2); 4.246(4.4); 4.232(5.2); 4.217(2.5);4.179(1.8); 4.164(3.1); 4.150(3.0); 4.135(2.9); 4.119(2.0); 4.104(5.1);4.088(6.8); 4.073(3.5); 4.067 (3.7); 4.058(2.9); 4.053(3.4); 4.045(3.0);4.039(3.2); 4.025(3.1); 3.910(1.6); 3.901(1.9); 3.881(2.0); 3.873(1.9);3.782(1.5); 2.541(0.7); 2.526(1.3); 2.512(1.4); 2.497(1.6); 2.490(2.2);2.476(1.9); 2.461(2.1); 2.448(1.4); 2.392(3.5); 2.367(3.7); 2.359 (3.1);2.347(3.5); 2.332(2.4); 2.323(2.1); 2.311(1.4); 2.286(1.5); 1.256(1.5);0.994(0.6); 0.974(1.6); 0.950(6.5); 0.930(16.0); 0.922(0.6); 0.910(7.9);0.611(0.7); 0.591(0.7); 0.547(2.5); 0.528(7.3); 0.508(6.7); 0.488(1.8);0.008(3.2); 0.000(91.7); −0.009(2.6) Example 289(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 7.518(15.3); 7.294(5.1); 7.260(2831.6); 7.227(5.7);7.209(4.0); 6.996(16.0); 1.537(809.6); 1.256(2.7); 0.146(3.8); 0.069(19.1); 0.008(40.2); 0.000(960.5); −0.008(36.7); −0.150(3.9) Example505(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.607(13.2); 8.526(13.9);8.513(14.5); 8.499(16.0); 7.520(1.2); 7.439(7.7); 7.426(7.6);7.327(2.9); 7.314(2.9); 7.295(0.9); 7.261(218.8); 7.251(2.0);7.239(1.9); 7.232(2.5); 7.224(1.9); 7.212(2.1); 7.207(3.3); 7.185(3.2);7.166(3.1); 7.161(3.1); 7.148(1.0); 7.142(2.9); 7.112(3.7); 7.091(4.5);7.066(3.7); 7.045(2.2); 6.997(2.6); 6.978(2.2); 6.955(1.4); 6.849(2.0);5.299 (12.2); 4.358(4.3); 4.342(4.9); 4.148(3.0); 4.132(3.5);4.038(1.4); 3.928(1.1); 3.918(1.4); 3.902(1.7); 3.890(1.4); 3.876(1.0);3.726(1.6); 3.712(1.8); 3.699(2.0); 3.614(1.4); 3.602(1.7); 3.587(1.6);3.498(1.7); 3.353(1.4); 2.280(0.6); 2.267(1.0); 2.244 (1.3); 2.232(1.8);2.216(1.6); 2.204(2.2); 2.192(1.7); 2.158(1.9); 2.149(1.8); 2.143(1.6);2.134(1.9); 2.127(2.4); 2.114(3.1); 2.102(2.4); 2.091(3.3); 2.079(2.4);2.067(1.2); 2.056(1.3); 2.043(0.7); 2.005(0.7); 1.586(1.7); 1.492(2.0);1.318(1.6); 1.255 (0.9); 0.008(2.6); 0.0064(1.0); 0.0056(1.0);0.005(1.1); 0.000(80.3); −0.006(0.8); -−0.007(0.7); −0.009(2.3) Example296(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.410(3.1); 8.403(7.8);8.396(5.2); 8.205(2.5); 7.969(4.4); 7.519(3.1); 7.373(2.2); 7.365(1.3);7.359(1.9); 7.353(1.7); 7.342 (1.5); 7.336(1.9); 7.331(1.5); 7.289(1.9);7.283(2.1); 7.278(1.7); 7.272(4.2); 7.260(579.5); 7.244(1.7);7.227(0.9); 7.209(0.9); 7.197(2.7); 7.191(2.8); 7.181(2.6); 7.175(2.6);7.121(1.2); 7.100(3.7); 7.093(2.9); 7.079(2.5); 7.072(6.5); 7.050(4.8);7.044 (1.2); 7.039(1.3); 7.033(1.1); 7.029(0.7); 7.023(0.6); 7.018(0.6);7.011(0.6); 6.996(3.3); 6.955(1.6); 6.949(1.6); 6.945(1.8); 6.939(1.6);6.934(1.3); 6.928(1.3); 6.923(1.2); 6.917(1.1); 5.299(16.0);4.286(3.44.271(3.9); 4.039(2.3); 4.022(2.5); 3.835 (0.9); 3.814(1.0);3.802(2.3); 3.788(2.2); 3.775(2.9); 3.762(1.3); 3.713(0.6); 3.703(0.8);3.687(1.0); 3.676(0.9); 3.672(0.8); 3.662(0.7); 3.561(1.2); 3.550(1.5);3.540(1.4); 3.535(1.3); 3.529(1.5); 3.523(1.2); 3.513(1.2); 3.502(1.1);3.440(1.1); 3.426 (1.5); 3.404(1.4); 3.387(1.2); 3.374(0.9); 3.360(0.9);3.347(0.7); 3.336(0.7); 2.615(1.1); 2.289(0.42.278(0.6); 2.264(0.7);2.254(0.9); 2.235(0.7); 2.229(0.8); 2.221(0.6); 2.213(1.5); 2.200(1.5);2.192(1.1); 2.186(1.0); 2.178(1.2); 2.170(0.9); 2.164 (0.8); 2.155(0.9);2.143(1.4); 2.131(1.3); 2.120(1.7); 2.107(1.5); 2.098(0.7); 2.087(0.9);2.071(0.8); 2.060(0.8); 2.053(0.6); 2.044(0.6); 2.025(0.6); 2.005(0.6);1.552(6.2); 1.333(0.9); 1.284(1.0); 1.259(0.9); 0.146(0.6); 0.113(0.8);0.008(6.2); 0.000 (194.3); −0.009(5.5); −0.150(0.6) Example 613(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.381(16.0); 8.369(1.42); 8.243(1.1);8.214(15.4); 7.519(5.4); 7.293(0.7); 7.289(0.8); 7.260(956.7);7.250(5.0); 7.244(2.3); 7.229(3.0); 7.226(3.7); 7.218(2.0); 7.209(3.2);7.205(3.4); 7.200(1.9); 7.185(2.0); 7.147(0.6); 7.128(1.3); 7.122(1.8);7.118 (1.4); 7.112(1.2); 7.101(1.3); 7.093(1.8); 7.087(1.4); 7.071(2.0);7.061(1.4); 7.050(3.1); 7.043(1.5); 7.030(1.9); 7.026(2.); 7.006(1.7);6.996(5.4); 6.921(1.6); 5.299(2.1); 4.265(4.0); 4.240(4.4); 4.184(3.4);4.157(4.4); 3.974(0.8); 3.965(0.8); 3.946(1.4); 3.936(1.4); 3.917(0.7);3.908(0.6); 3.887(0.8); 3.875(0.8); 3.861(1.4); 3.848(1.4); 3.836(0.9);3.823(0.7); 3.779(0.9); 3.766 (1.4); 3.753(1.8); 3.740(1.8); 3.726(1.1);3.636(1.0); 3.623(1.6); 3.610(2.0); 3.597(2.0); 3.583(1.2); 3.478(0.9);3.467(1.1); 3.456(1.2); 3.444(1.2); 3.428(1.0); 3.411(1.0); 3.399(1.1);3.388(1.2); 3.377(1.2); 3.362(0.9); 3.350(0.9); 2.544(0.6); 2.535 (0.9);2.522(1.0); 2.510(1.0); 2.499(1.3); 2.490(0.7); 2.476(0.6); 2.294(0.8);2.266(0.9); 2.231(0.7); 2.040(1.1); 2.013(0.9); 2.005(0.7); 1.936(0.7);1.923(1.0); 1.912(0.9); 1.901(1.4); 1.888(1.2); 1.878(0.7); 1.865(0.7);1.543(11.9); 1.371(0.9); 1.333 (1.7); 1.284(2.4); 1.256(2.2);0.146(1.0); 0.008(9.1); 0.000(336.9); −0.009(9.9); −0.150(1.0) Example289 threo2(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.393(7.4); 8.195(7.2);7.521(1.0); 7.295(0.6); 7.262(185.3); 7.246(6.1); 7.155(4.0);7.134(7.9); 7.131(5.5); 7.114(6.1); 7.110 (7.9); 7.090(5.1); 7.083(4.2);7.078(4.3); 7.065(4.4); 7.059(5.5); 7.051(4.4); 7.039(4.0); 7.033(4.0);6.998(1.1); 6.918 (4.2); 6.914(5.2); 6.909(4.4); 6.903(3.9); 6.897(3.7);6.892(4.3); 6.888(3.4); 5.299(16.0); 4.046(10.1); 4.028(10.6);3.708(2.7); 3.697(3.8); 3.694(3.8); 3.682(5.1); 3.671(4.4); 3.667(4.2);3.657(3.2); 3.483(2.2); 3.474(2.6); 3.466(2.7); 3.456(4.3); 3.447 (2.9);3.439(2.6); 3.429(2.1); 3.391(3.0); 3.380(3.4); 3.367(4.6); 3.356(4.6);3.341(2.9); 3.330(2.7); 2.324(1.3); 2.310(1.7); 2.300(2.6); 2.289(3.2);2.276(3.3); 2.265(3.4); 2.255(2.2); 2.241(1.5); 2.096(1.7); 2.086(3.2);2.075(2.1); 2.069(2.1); 2.058 (3.9); 2.050(3.4); 2.040(1.6); 2.033(1.6);2.023(2.3); 2.012(1.2); 1.622(3.8); 1.333(0.8); 1.284(1.1); 1.256(1.6);0.008(2.0); 0.000(64.2); −0.006(0.6); −0.007(0.5); −0.009(1.8) Example86(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.399(5.2); 8.392(5.9);8.388(7.3); 8.381(7.0); 8.213(3.8); 7.967(6.9); 7.519(1.3); 7.347(2.5);7.342(3.2); 7.336(2.6); 7.324 (2.9); 7.319(4.3); 7.313(4.2); 7.305(3.8);7.295(5.5); 7.290(4.5); 7.285(7.2); 7.280(10.6); 7.277(8.4);7.260(230.5); 7.250 (9.2); 7.242(3.1); 7.231(7.3); 7.226(3.4);7.221(4.7); 7.216(2.8); 7.211(3.4); 7.175(1.0); 7.137(4.4); 7.133(7.2);7.128(3.9); 7.061(2.7); 7.042(2.0); 6.996(1.8); 6.959(3.8); 6.940(3.4);5.299(16.0); 4.491(0.6); 4.477(0.6); 4.278(5.6); 4.263(5.8); 4.038(3.3); 4.021(3.5); 3.835(1.0); 3.802(1.5); 3.789(3.1); 3.776(3.2);3.762(3.8); 3.749(1.9); 3.695(0.9); 3.684(1.4); 3.669(1.6); 3.658(1.3);3.654(1.2); 3.643(1.2); 3.553(1.7); 3.542(2.0); 3.532(2.1); 3.526(1.8);3.520(2.1); 3.515(1.7); 3.505(1.6); 3.493 (2.0); 3.473(0.9); 3.463(2.2);3.447(2.7); 3.437(2.1); 3.425(2.2); 3.408(1.1); 3.389(1.0); 3.377(1.0);3.365(1.3); 3.353(1.3); 3.339(0.9); 3.327(0.8); 2.964(0.8); 2.945(0.8);2.911(0.5); 2.315(0.5); 2.300(0.6); 2.291(0.9); 2.281(1.0); 2.266(1.0);2.25 (1.4); 2.240(1.4); 2.232(1.3); 2.225(0.9); 2.218(2.1); 2.204(2.5);2.196(1.5); 2.190(1.5); 2.183(1.9); 2.168(1.2); 2.158(1.3); 2.145(2.3);2.134(2.0); 2.122(2.7); 2.110(2.5); 2.099(1.8); 2.087(1.4); 2.074(1.4);2.065(0.9); 2.048(0.6); 2.037(0.8); 1.570 (1.7); 1.371(1.1); 1.333(0.9);1.286(1.7); 1.257(2.5); 0.880(0.5); 0.008(3.5); 0.000(88.5); −0.009(3.7)Example 619(Ibab): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.421(9.4);8.250(10.9); 7.595(1.5); 7.590(1.6); 7.580(1.5); 7.574(1.5); 7.417(1.6);7.411(1.7); 7.401(1.6); 7.396(1.6); 7.328 (0.7); 7.322(0.7); 7.317(0.8);7.311(0.7); 7.307(1.1); 7.301(1.1); 7.296(1.1); 7.290(1.0); 7.261(61.7);7.217(1.9); 7.196(2.6); 7.176(1.3); 7.113(0.7); 7.107(0.7); 7.102(0.8);7.096(0.8); 7.092(1.1); 7.086(1.1); 7.081(1.1); 7.075(0.9); 7.019(2.2);6.999 (3.0); 6.978(1.4); 4.267(0.6); 4.254(1.3); 4.239(1.2); 4.225(1.7);4.216(2.4); 4.190(2.5); 4.164(2.5); 4.136(3.1); 4.117(1.3); 4.102(1.2);4.088(1.5); 4.075(0.9); 4.046(0.9); 4.034(1.0); 4.024(1.1); 4.017(0.9);4.012(1.0); 4.006(0.8); 3.995(0.7); 3.983 (0.7); 3.961(16.0);3.926(14.2); 3.908(0.8); 3.901(0.7); 3.896(0.8); 3.890(0.6);3.879(0.43.868(0.6); 3.845(0.6); 3.836(0.6); 3.817(1.0); 3.807(1.0);3.789(0.5); 3.779(0.5); 3.769(0.5); 3.741(0.8); 3.731(0.8); 2.682(0.6);2.669(0.8); 2.659(0.8); 2.646 (0.8); 2.637(0.5); 2.464(0.5); 2.437(0.6);2.183(0.6); 2.015(0.6); 2.004(0.6); 1.992(0.7); 1.980(0.7); 1.586(0.6);1.255(0.7); 0.008(0.8); 0.000(23.4); −0.008(0.8) Example 599(Ibae):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.409(5.4); 8.215(5.9); 7.400(1.0);7.396(2.3); 7.394(2.0); 7.392(1.5); 7.378(3.0); 7.274(0.8); 7.269(1.2);7.261(39.2); 7.252 (1.0); 7.247(0.6); 7.242(0.5); 7.240(0.5);7.237(0.6); 7.226(0.7); 7.222(1.0); 7.221(1.3); 7.217(1.1); 7.196(2.7);7.177(1.7); 7.157(0.7); 7.052(0.9); 7.033(0.7); 4.214(1.4); 4.206(0.7);4.188(1.8); 4.177(0.9); 4.163(1.7); 4.135(1.7); 4.058(0.6); 4.043 (0.6);4.029(1.2); 4.016(0.7); 3.922(8.4); 3.889(0.5); 3.882(4.2); 3.878(4.3);3.849(0.5); 3.822(0.5); 3.812(0.5); 3.407(16.0); 3.387(14.7);0.000(14.8) Example 289 threo 1(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.395(14.8); 8.389(14.9); 8.193(14.6); 7.521(1.2); 7.295(0.8);7.285(0.6); 7.284(0.6); 7.283(0.6); 7.2823(0.5); 7.2815(0.5);7.281(0.6); 7.2783(0.9); 7.2775(0.9); 7.277(1.0); 7.276(1.2);7.272(6.5); 7.2663(10.5); 7.2655(11.5); 7.262 (205.0); 7.256(2.0);7.255(1.7); 7.254(1.5); 7.253(1.4); 7.252(1.4); 7.249(5.9); 7.244(7.3);7.238(5.5); 7.155(5.5); 7.134(9.2); 7.131(6.3); 7.114(7.2); 7.110(9.2);7.089(6.6); 7.083(5.1); 7.077(5.3); 7.065(5.2); 7.059(6.1); 7.057(6.0);7.050(5.4); 7.038 (4.9); 7.032(5.1); 6.998(1.2); 6.923(3.3); 6.918(4.3);6.913(6.2); 6.908(4.4); 6.902(4.4); 6.897(3.7); 6.892(5.0); 6.887(3.5);6.882(2.5); 5.299(8.7); 4.045(15.0); 4.027(16.0); 3.708(4.0);3.698(4.8); 3.694(4.9); 3.682(6.6); 3.671(5.8); 3.667(5.6); 3.657 (4.8);3.482(2.7); 3.472(2.9); 3.464(2.8); 3.454(5.3); 3.445(3.1); 3.437(2.9);3.427(2.6); 3.391(4.8); 3.380(5.6); 3.367(6.2); 3.365(5.4); 3.356(6.1);3.353(5.8); 3.341(4.8); 3.329(4.4); 2.323(2.1); 2.313(2.3); 2.309(2.5);2.299(4.3); 2.288(4.4); 2.285 (2.9); 2.278(3.4); 2.274(4.4); 2.264(5.6);2.254(3.1); 2.250(2.9); 2.240(2.6); 2.096(2.7); 2.085(5.0); 2.074(2.9);2.068(2.8); 2.058(5.3); 2.050(4.3); 2.047(3.4); 2.039(2.1); 2.033(2.2);2.022(3.7); 2.011(1.9); 1.592(5.5); 1.333(1.0); 1.284(1.4); 1.255 (1.6);0.008(2.0); 0.000(66.6); −0.009(2.0) Example 512(Iba): ¹H-NMR (400.0MHz. CDCl₃): δ = 8.564(1.2); 8.544(11.3); 8.529(3.7); 8.495(16.0);8.471(1.0); 8.440(0.7); 8.425(1.0); 8.412(7.1); 8.400(7.1); 8.393(2.6);8.381(2.6); 8.372(10.3); 8.360(10.3); 7.521(0.9); 7.500(4.9);7.495(5.3); 7.484(5.1); 7.478(5.3; 7.453(3.8); 7.447(4.1); 7.436 (3.9);7.430(4.1); 7.373(0.8); 7.333(3.3); .327(3.3); 7.322(3.5); 7.316(3.6);7.311(4.6); 7.305(4.5); 7.300(4.5); 7.294(4.6); 7.286(3.0); 7.281(3.3);7.275(3.5); 7.270(5.2); 7.262(109.3); 7.254(4.7); 7.242(1.5);7.219(6.0); 7.202(11.1); 7.198(12.8); 7.187(8.0); 7.181(12.3);7.176(4.7); 7.160(5.4); 7.127(0.7); 7.105(8.9); 7.092(8.6); 6.998(0.8);5.299(5.0); 4.417(7.0); 4.402 (7.1); 4.052(5.4); 4.034(5.5); 3.868(0.5);3.851(0.5); 3.811(3.1); 3.801(3.1); 3.784(3.4); 3.773(3.4); 3.727(0.5);3.690(13.9); 3.564(3.2); 3.546(3.4); 3.537(5.8); 3.519(6.0); 3.501(3.9);3.489(4.1); 3.481(6.1); 3.472(8.7); 3.462(3.5); 3.454(3.5); 3.445 (3.1);3.090(1.7); 3.071(3.2); 3.051(2.1); 3.021(3.2); 3.011(3.4); 2.987(4.8);2.977(4.8); 2.885(1.8); 2.866(5.4); 2.852(4.7); 2.838(5.9); 2.827(7.5);2.811(5.2); 2.804(4.4); 2.792(1.7); 2.777(1.4); 2.702(2.3); 2.683(3.6);2.664(1.9); 2.494(0.9); 2.483 (1.5); 2.470(2.0); 2.465(1.9); 2.460(2.2);2.451(2.2); 2.446(1.9); 2.441(2.4); 2.430(2.3); 2.422(2.0); 2.413(2.7);2.404(2.5); 2.397(2.6); 2.387(2.4); 2.379(1.5); 2.370(1.3); 2.360(0.7);1.840(1.0); 1.255(0.5); 0.008(1.6); 0.000(40.9); −0.009(1.7) Example619(Ibab): ¹H-NMR (400.0 MHz. CDCl₃): δ = 8.421(9.4); 8.250(10.9);7.595(1.5); 7.590(1.6); 7.580(1.5); 7.574(1.5); 7.417(1.6); 7.411(1.7);7.401(1.6); 7.396(1.6); 7.328 (0.7); 7.322(0.7); 7.317(0.8); 7.311(0.7);7.307(1.1); 7.301(1.1); 7.296(1.1); 7.290(1.0); 7.261(61.7); 7.217(1.9);7.196(2.6); 7.176(1.3); 7.113(0.7); 7.107(0.7); 7.102(0.8); 7.096(0.8);7.092(1.1); 7.086(1.1); 7.081(1.1); 7.075(0.9); 7.019(2.2); 6.999 (3.0);6.978(1.4); 4.267(0.6); 4.254(1.3); 4.239(1.2); 4.225(1.7); 4.216(2.4);4.190(2.5); 4.164(2.5); 4.136(3.1); 4.117(1.3); 4.102(1.2); 4.088(1.5);4.075(0.9); 4.046(0.9); 4.034(1.0); 4.024(1.1); 4.017(0.9); 4.012(1.0);4.006(0.8); 3.995(0.7); 3.983 (0.7); 3.961(16.0); 3.926(14.2);3.908(0.8); 3.901(0.7); 3.896(0.8); 3.890(0.6); 3.879(0.43.868(0.6);3.845(0.6); 3.836(0.6); 3.817(1.0); 3.807(1.0); 3.789(0.5); 3.779(0.5);3.769(0.5); 3.741(0.8); 3.731(0.8); 2.682(0.6); 2.669(0.8); 2.659(0.8);2.646 (0.8); 2.637(0.5); 2.464(0.5); 2.437(0.6); 2.183(0.6); 2.015(0.6);2.004(0.6); 1.992(0.7); 1.980(0.7); 1.586(0.6); 1.255(0.7); 0.008(0.8);0.000(23.4); −0.008(0.8) Example 6198(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ= 8.384(14.1); 8.219(16.0); 7.588(2.5); 7.582(2.7); 7.572(2.6);7.566(2.7); 7.519(1.1); 7.431(2.4); 7.425(2.6); 7.415(2.47.);7.410(2.6); 7.325(1.3); 7.319(1.3); 7.314(1.5); 7.308(1.4); 7.304(1.9);7.298(1.9); 7.293(2.0); 7.287(1.7); 7.260(176.1); 7.191 (3.4);7.170(4.9); 7.150(2.8); 7.122(1.3); 7.116(1.2); 7.111(1.3); 7.105(1.3);7.101(1.7); 7.095(1.7); 7.089(1.7); 7.084(1.6); 7.010(3.9); 6.996(1.3);6.990(5.2); 6.969(2.6); 4.258(3.45); .233(4.0); 4.176(3.8); 4.148(4.9);3.972(0.9); 3.962(0.9); 3.944 (1.5); 3.935(1.5); 3.917(0.7); 3.907(0.7);3.879(0.8); 3.867(0.8); 3.853(1.4); 3.841(1.4); 3.828(0.8); 3.816(0.7);3.780(1.1); 3.767(1.7); 3.753(2.0); 3.740(2.0); 3.727(1.3); 3.632(1.0);3.619(1.6); 3.606(2.1); 3.593(2.0); 3.580(1.3); 3.477(1.2); 3.466 (1.3);3.454(1.4); 3.450(1.3); 3.443(1.4); 3.439(1.3); 3.427(1.2); 3.415(1.1);3.409(1.2); 3.397(1.2); 3.386(1.3); 3.382(1.1); 3.375(1.3); 3.371(1.1);3.360(1.0); 3.348(1.0); 2.553(0.6); 2.543(0.6); 2.539(0.6); 2.530(1.0);2.518(1.1); 2.507(1.1); 2.495 (1.2); 2.485(0.8); 2.482(0.8); 2.472(0.6);2.297(0.9); 2.282(0.6); 2.270(1.0); 2.266(0.9); 2.262(0.9); 2.258(0.8);2.234(0.7); 2.071(0.7); 2.059(0.5); 2.047(0.8); 2.044(0.9); 2.036(1.1);2.021(0.8); 2.009(0.9); 1.997(0.5); 1.928(0.7); 1.915(1.0); 1.904 (0.9);1.893(1.3); 1.880(1.2); 1.870(0.7); 1.858(0.7); 1.845(0.5); 1.672(0.8);1.621(0.6); 0.008(2.0); 0.000(66.8); −0.009(2.0) Example 208 threo(Iba):¹H-NMR (400.0 MHz. CDCl₃): δ = 8.574(1.9); 8.570(2.0); 8.563(2.0);8.559(2.0); 8.519(10.6); 8.515(11.0); 8.508(10.9); 8.504(10.9);7.723(2.4); 7.720(2.4); 7.703(2.6); 7.699(2.5); 7.538(13.3);7.534(13.7); 7.517(15.0); 7.513(14.7); 7.261(206.1); 7.223(2.7);7.217(0.9); 7.211(3.7); 7.202(3.2); 7.199(1.0); 7.191(3.4); 7.182(1.6);7.178(1.0); 7.172(0.9); 7.167(1.1); 7.162(1.4); 7.157(1.5); 7.138(1.2);7.112 (16.2); 7.100(15.5); 7.091(14.3); 7.080(14.1); 7.024(4.2);7.003(7.8); 7.000(5.1); 6.995(4.9); 6.989(5.3); 6.983(6.); 6.978 (9.3);6.971(5.7); 6.968(5.2); 6.962(5.5); 6.958(6.5); 6.950(4.2); 6.944(4.8);6.909(3.6); 6.905(3.9); 6.903(3.7); 6.899(5.6); 6.895(4.2); 6.893(3.7);6.889(3.7); 6.884(2.9); 6.877(3.7); 6.874(2.7); 6.868(2.1); 4.366(12.7);4.360(2.8); 4.341(16.0); 4.160 (4.3); 4.143(7.2); 4.134(4.0);4.126(4.6); 4.117(5.6); 4.109(1.8); 4.100(3.6); 4.085(0.7); 3.631(3.3);3.617(6.8); 3.603(8.4); 3.589(9.6); 3.575(4.9); 3.523(0.6); 3.509(1.1);3.495(1.5); 3.488(5.1); 3.481(2.1); 3.472(7.5); 3.461(3.9); 3.454(5.6);3.443 (5.1); 3.427(3.7); 3.412(1.0); 3.398(1.1); 3.392(1.1); 3.384(0.7);3.378(1.1); 3.371(0.7); 3.364(0.7); 3.351(0.6); 2.409(8.5); 2.393(12.7);2.377(12.6); 2.361(7.8); 2.093(0.7); 2.069(0.8); 2.058(1.5); 2.048(0.5);2.045(0.5); 2.034(0.9); 1.873(0.5); 1.868 (0.6); 1.864(0.6); 1.858(0.6);1.853(0.6); 1.849(0.8); 1.838(0.8); 1.607(3.5); 0.008(2.1); 0.000(77.2);−0.009(2.2) Example 1693(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.012(0.8); 7.261(52.9); 7.160(0.8); 7.156(1.4); 7.139(1.4); 7.135(3.0);7.131(1.6); 7.118(1.47.115(2.8); 7.110(2.3); 7.094 (1.0); 7.090(1.6);7.086(0.7); 7.080(0.7); 7.068(0.6); 7.062(0.8); 7.059(0.7); 7.053(0.7);7.041(0.6); 7.035(0.7); 7.025(1.1); 7.019(1.3); 7.007(1.2); 7.001(1.4);6.998(1.4); 6.992(1.3); 6.980(1.1); 6.974(1.3); 6.963(0.6); 6.958(0.8);6.954(0.6); 6.948 (0.6); 6.937(0.6); 6.926(0.9); 6.921(1.1); 6.915(1.4);6.911(1.1); 6.905(1.1); 6.899(0.9); 6.894(1.2); 6.889(0.8); 6.885(0.6);6.377(3.2); 6.368(5.6); 6.359(3.7); 6.279(4.2); 6.275(4.3); 6.269(3.5);6.265(3.5); 6.257(2.2); 6.252(2.2); 6.247(1.9); 6.242 (1.48); .144(3.5);4.130(3.6); 3.951(1.9); 3.933(2.0); 3.821(1.0); 3.808(2.2); 3.795(2.1);3.781(2.9); 3.769(1.5); 3.762(0.7) 3.757(0.6); 3.745(0.8); 3.735(0.8);3.730(0.8); 3.720(0.7); 3.655(1.4); 3.643(1.5); 3.633(1.6); 3.628(1.2);3.622(1.6); 3.616 (1.2); 3.606(1.2); 3.595(1.1); 3.563(0.7); 3.551(0.8);3.539(0.9); 3.536(0.7); 3.528(0.9); 3.525(0.8); 3.512(0.7); 3.501(0.6);3.488(1.2); 3.437(0.7); 3.432(1.1); 3.424(1.4); 3.418(1.3); 3.408(1.2);3.404(1.0); 3.400(1.2); 3.394(1.0); 3.386(0.5); 2.957 (7.8); 2.956(7.8);2.882(6.7); 2.881(6.7); 2.264(0.6); 2.229(0.7); 2.137(0.7); 2.115(1.4);2.102(2.0); 2.094(1.1); 2.088(1.0); 2.080(1.8); 2.078(1.3); 2.066(2.2);2.053(1.8); 2.042(1.9); 2.030(1.4); 2.018(0.7); 2.005(16.0); 1.943(0.6);1.915(0.6); 1.908 (0.5); 1.462(2.5); 0.008(0.6); 0.000(19.5);−0.009(0.6) Example 1700(Iba): ¹H-NMR (400.0 MHz. CDCl₃): δ =8.005(1.8); 7.291(3.2); 7.285(3.4); 7.274(3.2); 7.269(3.7); 7.262(60.2);7.230(6.1); 7.224(6.4); 7.213(6.3); 7.207(6.3); 7.123 (1.7); 7.116(5.3);7.102(6.4); 7.094(14.3); 7.086(3.5); 7.081(7.6); 7.073(11.9);7.069(3.7); 7.065(1.2); 7.059(1.0); 7.053 (0.8); 7.044(4.5); 7.038(4.3);7.032(4.8); 7.027(4.4); 7.022(2.8); 7.016(2.5); 7.011(2.4); 7.005(2.2);6.998(0.5); 6.378(3.1); 6.377(3.1); 6.373(5.8); 6.372(5.8); 6.369(6.4);6.364(10.8); 6.355(6.5); 6.282(10.0); 6.278(10.1); 6.272(8.2);6.268(8.1); 6.261 (5.1); 6.256(5.1); 6.251(4.3); 6.247(4.2); 4.138(9.2);4.124(9.5); 3.950(5.1); 3.931(5.5); 3.819(2.4); 3.806(5.3); 3.792(5.1);3.779(7.2); 3.770(1.8); 3.766(3.6); 3.761(1.7); 3.756(1.6); 3.744(2.1);3.734(1.9); 3.729(1.9); 3.719(1.7); 3.653(3.3); 3.641 (3.7); 3.632(3.8);3.626(2.9); 3.620(3.8); 3.614(2.9); 3.605(2.8); 3.593(2.6); 3.562(1.7);3.550(1.9); 3.538(2.1); 3.535(1.7); 3.526(2.1); 3.523(1.8); 3.511(1.6);3.499(1.4); 3.485(6.8); 3.458(0.7); 3.450(1.0); 3.441(1.0); 3.433(2.1);3.429(2.2); 3.420 (3.2); 3.413(3.5); 3.404(3.2); 3.396(3.3); 3.390(2.6);3.381(1.3); 3.375(1.2); 2.958(16.0); 2.880(13.4); 2.879(12.9);2.281(0.7); 2.272(0.7); 2.267(0.8); 2.258(1.5); 2.247(1.2); 2.243(0.9);2.237(1.0); 2.232(1.2); 2.223(1.8); 2.214(0.9); 2.208(0.9); 2.199 (0.8);2.146(0.8); 42.133(1.7); 2.125(0.9); 2.120(1.1); 2.111(3.5); 2.098(4.8);2.090(2.8); 2.085(2.4); 2.077(4.2); 2.071(2.5); 2.063(2.5); 2.059(4.6);2.047(4.3); 2.035(4.6); 2.023(3.4); 2.012(1.7); 2.000(1.7); 1.988(0.8);1.952(0.9); 1.941(1.4); 1.930 (0.9); 1.923(0.9); 1.917(1.); 1.913(1.5);1.906(1.3); 1.902(1.0); 1.896(0.8); 1.888(0.8); 1.878(1.1); 1.867(0.7);1.489(10.1); 0.008(0.7); 0.000(22.5); −0.009(0.7)

The retention time (Rt) given in the Rt table below for the enantiomerof the formula (Ia) in question is given in minutes (min), where theletter a, b, c or d given after the forward slash after the retentiontime refers to the conditions stated above for HPLC on a chiral columnand the respective mobile phase stated above, i.e. mobile phase a,mobile phase b, mobile phase c or mobile phase d.

Rt Table: Rt in min.

No. Q(R²)_(n) (R³)_(m) erythro-1 erythro-2 threo-1 threo-2 289a 3,4-F₂5-fluoropyridin- 7.070/c 7.385/c 11.894/c 14.023/c 3-yl

Formulation Examples

-   -   a) A dust is obtained by mixing 10 parts by weight of a compound        of the formula (I) and 90 parts by weight of talc as inert        substance and comminuting the mixture in a hammer mill.    -   b) A wettable powder which is readily dispersible in water is        obtained by mixing 25 parts by weight of a compound of the        formula (I), 64 parts by weight of kaolin-containing quartz as        inert substance, 10 parts by weight of potassium lignosulfonate        and 1 part by weight of sodium oleoylmethyltaurate as wetting        agent and dispersant, and grinding the mixture in a pinned-disk        mill.    -   c) A readily water-dispersible dispersion concentrate is        obtained by mixing 20 parts by weight of a compound of the        formula (I) with 6 parts by weight of alkylphenol poly glycol        ether (®Triton X 207), 3 parts by weight of isotridecanol        polyglycol ether (8 EO) and 71 parts by weight of paraffinic        mineral oil (boiling range for example about 255 to about 277°        C.) and grinding the mixture in a ball mill to a fineness of        below 5 microns.    -   d) An emulsifiable concentrate is obtained from 15 parts by        weight of a compound of the formula (I), 75 parts by weight of        cyclohexanone as solvent and 10 parts by weight of oxyethylated        nonylphenol as emulsifier.    -   e) Water-dispersible granules are obtained by mixing

75 parts by weight of a compound of the formula (I), 10 parts by weightof calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin,

-   -   -   grinding the mixture in a pinned-disk mill, and granulating            the powder in a fluidized bed by spray application of water            as a granulating liquid.

    -   f) Water-dispersible granules are also obtained by homogenizing        and precomminuting, in a colloid mill,

25 parts by weight of a compound of the formula (I), 5 parts by weightof sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, 2 parts by weight ofsodium oleoylmethyltaurinate, 1 part by weight of polyvinyl alcohol, 17parts by weight of calcium carbonate and 50 parts by weight of water,

-   -   -   then grinding the mixture in a bead mill and atomizing and            drying the resulting suspension in a spray tower by means of            a one-phase nozzle.

BIOLOGICAL EXAMPLES Example PE Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantswere placed in wood-fiber pots in sandy loam and covered with soil. Thecompounds (I) according to the invention, formulated in the form ofwettable powders (WP), were then applied as aqueous suspension oremulsion at a water application rate of 600 l/ha (converted) with theaddition of 0.2% of wetting agent to the surface of the covering soil.

After the treatment, the pots were placed in a greenhouse and kept undergood growth conditions for the test plants. After about 3 weeks, theeffect was scored visually in comparison with untreated controls aspercentages. For example, 100% activity=the plants have died, 50%herbicidal activity or damage=the plants have been reduced by 50% or theplant mass has been reduced by 50%, 0% activity=like control plants.

The results obtained show that compounds (I) according to the inventionand their salts, in particular the compounds according to the inventioncharacterized as preferred, have good to very good pre-emergenceherbicidal activity against harmful plants at an application rate of 320g or less per hectare, generally also even at a respective applicationrate of 80 g/ha.

The biological tests were carried out in each case separately with thecompounds according to the invention below which, by virtue of the goodto very good herbicidal activity thereof, are particularly preferredaccording to the invention:

Compound No. 532a threo, 532a erythro, 1288a, 1272a, 1295a, 208 threo,208a, 208a threo, 215a, 1477a, 1461a, 1484a, 1542a, 1558a, 1565a, 1677a,1531a, 1515a, 1538a, 181a, 647a, 1153a, 1137a, 1516a, 289a, 289 threo-1,289 erythro-1, 100a, 107a, 296a, 613a, 620a, 86a, 597a, 512a, 599a and599bae.

Here, these compounds according to the invention were in each caseemployed in the biological tests as a component of a wettable powder (WPformulation).

At an application rate of 320 g/ha, all the compounds according to theinvention mentioned showed 80% to 100% herbicidal activity in thebiological tests, against one, more than one or all of the harmfulplants below:

ALOMY=Alopecurus myosuroides

AVEFA=Avena fatua

CYPES=Cyperus esculentus

ECHCG=Echinochloa crus-galli

LOLMU=Lolium multiflorum

SETVI=Setaria viridis

ABUTH=Abutilon theophrasti

AMARE=Amaranthus retroflexus

POLCO=Polygonum convolvulus (=Fallopia convolvulus)

STEME=Stellaria media

VIOTR=Viola tricolor

VERPE=Veronica persica

What was determined was the respective herbicidal activity, in each caseat the same point in time after application of the formulation inquestion, i.e. the damage to the respective harmful plant in %.

Furthermore, the compounds according to the invention mentioned abovewere applied to the following useful plants, in each case at theapplication rates mentioned.

ORYSA=Oryza sativa (common rice)

TRZAS=triticum aestivum (spring) (summer wheat)

ZEAMX=Zea mays (maize)

BRSNW=Brassica napus subsp. napus (winter) (winter oilseed rape)

Here, the observed damage to said useful plants was in each case withinthe acceptable range and was generally assessed as low (generally in therange from 0 to 20%, mostly in the range from 0 to 10%).

Example PO Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weeds and crop plants wereplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants were treated at the one-leaf stage, wherethe compounds according to the invention, formulated in the form ofwettable powders (WP), were applied by spraying as aqueous suspension oremulsion at a water application rate of 600 l/ha (converted) with theaddition of 0.2% of wetting agent to the green parts of the plants.After the test plants had been kept in the greenhouse under optimumgrowth conditions for about 3 weeks, the activity of the preparationswas rated visually in comparison to untreated controls in percent (%).For example, 100% activity=the plants have died, 50% herbicidal activityor damage=the plants have been reduced by 50% or the plant mass has beenreduced by 50%, 0% activity=like control plants.

The biological tests were in each case carried out separately using thecompounds according to the invention below which are particularlypreferred according to the invention by virtue of their good to verygood herbicidal activity:

Compound No. 532a threo, 1288a, 1542a, 1558a, 1700, 1700a, 1531a, 151a,1538a, 181a, 647a, 1516a, 289a, 289 erythro-1, 289 threo-2, 100a, 107a,296a, 613a, 620a, 86a, 84a, 295a, 599a, 599bae, 619, 6191bab, 619a and619bab.

The results obtained show that compounds (I) according to the inventionand their salts, in particular the compounds according to the inventionmentioned as being preferred, have good to very good post-emergenceherbicidal activity against harmful plants at an application rate of 320g or less per hectare, frequently even at a respective application rateof 80 g/ha.

At an application rate of 320 g/ha, all of the compounds according tothe invention mentioned show, in the biological tests, 80% to 100%herbicidal activity against one, more than one or all of the harmfulplants mentioned in the above biological example PE. In each case, as inthe above biological example PE, the observed damage of the crop plantsORYSA, TRZAS, ZEAMX and BRSNW was likewise in the acceptable range.

The invention claimed is:
 1. A compound of the formula (I) or saltthereof,

in which Q represents a mono- or bicyclic heteroaromatic radical with intotal 1 to 9 carbon ring atoms, where the heteroatom or heteroatoms inthe heteroaromatic ring are selected from the group consisting of N, O,S, P, B, Si, and Se, R¹ represents hydrogen or a hydrolyzable radical,(R²)_(n) represent n substituents R², where R² (if n=1) or each of thesubstituents R² (if n is greater than 1) independently of one anotherrepresents halogen, cyano, nitro, (C₁-C₈)alkyl, (C₁-C₈)alkoxy,(C₁-C₈)alkylthio, (C₁-C₈)alkylsulfinyl, (C₁-C₈)alkylsulfonyl,(C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl, (C₁-C₆)haloalkoxy,(C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,tri-[(C₁-C₄)alkyl]silyl or tri-[(C₁-C₄)alkyl]silyl-(C₁-C₄)alkyl, or ineach case two R² directly adjacent on the heteroaromatic radical Q aretogether a group of the formula —Z¹-A*¹—Z²—, in which A* represents analkylene group having 1 to 4 carbon atoms which is optionallysubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and(C₁-C₄)haloalkoxy, Z¹ represents a direct bond, 0 or S and Z² representsa direct bond, 0 or S, where the group —Z¹-A*-Z²— together with theatoms of the heteroaromatic radical Q bonded to this group Q form a 5-or 6-membered ring, and (R³)_(m) represents m substituents R³, where R³(if m=1) or each of the substituents R³ (if m is greater than 1)independently of one another represents halogen, cyano, nitro,(C₁-C₈)alkyl, (C₁-C₈)alkoxy, (C₁-C₈)alkylthio, (C₁-C₈)alkylsulfinyl,(C₁-C₈)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,(C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₄)alkyl or—NR*R**, where R* and R**, independently of one another andindependently of any other radicals —NR*R** present, are in each caseselected from the group consisting of H, (C₁-C₈)alkyl, (C₂-C₈)alkenyl,(C₂-C₈)alkynyl, (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)alkanoyl,[(C₁-C₄)haloalkyl]carbonyl, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)haloalkoxy]carbonyl, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkenyl,(C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl, phenyl and phenyl-(C₁-C₄)alkyl, whereeach of the specified radicals (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkyl-(C₁-C₄)alkyl, (C₃-C₆)cycloalkenyl,(C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl, phenyl and phenyl-(C₁-C₄)alkyl issubstituted in the cycle optionally by one or more identical ordifferent radicals R^(bb), where R^(bb) in each case represents halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or (C₁-C₄)haloalkoxy and,in the case of (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkyl-(C₁-C₄)alkyl,(C₃-C₆)cycloalkenyl, (C₃-C₆)cycloalkenyl-(C₁-C₄)alkyl, R^(bb) mayadditionally represent oxo, or NR*R** represents a 3- to 8-memberedheterocycle which, in addition to this nitrogen atom, optionallycontains one or two further ring heteroatoms selected from the groupconsisting of N, O and S and which is unsubstituted or substituted byone or more radicals selected from the group consisting of (C₁-C₄)alkyl,(C₁-C₄)haloalkyl and oxo, or where in each case two groups R³ directlyadjacent on the ring together represent a group of the formula—Z³-A**-Z⁴—, in which A** represents an alkylene group having 1 to 4carbon atoms which is optionally substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and (C₁-C₄)haloalkoxy, Z³ represents adirect bond, O or S and Z⁴ represents a direct bond, 0 or S, where thegroup —Z³-A**-Z⁴ together with the carbon atoms, bonded to this group,of the phenyl ring form a 5- or 6-membered ring, n represents 0, or aninteger in the range from 1 to 5, and m represents 0, 1, 2, 3, 4 or 5.2. The compound of the formula (I) or salt thereof according to claim 1,wherein Q represents a mono- or bicyclic heteroaromatic radical havingin total 2 to 9 carbon ring atoms, where the heteroaromatic radical Qcontains 1, 2, 3 or 4 heteroatoms in the heteroaromatic ring and theheteroatom or the heteroatoms are selected from the group consisting ofN, O, and S.
 3. The compound of the formula (I) or salt thereof asclaimed in claim 1, wherein Q represents a mono- or bicyclicheteroaromatic radical selected from the group consisting ofpyrimidinyl, pyridinyl, pyridazinyl, pyrazinyl, thienyl, furyl,oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazinyl, quinolyl,isoquinolyl, cinnolinyl-, quinazolinyl, quinoxalinyl, pteridinyl,indolyl and phthalazinyl.
 4. The compound of the formula (I) or saltthereof as claimed in claim 1, wherein the compound of the formula (I)corresponds to the formula (I-1), (I-2) or (I-3) defined below

where R¹, R², R³, m and n have the meaning defined in claim
 1. 5. Thecompound of the formula (I) or salt thereof as claimed in claim 1,wherein R¹ represents hydrogen or a hydrolyzable radical having in totalup to 30 carbon atoms.
 6. The compound of the formula (I) or saltthereof as claimed in claim 1, wherein R¹ represents hydrogen or ahydrolyzable radical having in total 1 to 24 carbon atoms, where R¹represents an optionally substituted hydrocarbon radical or anoptionally substituted heterocyclyl radical, or represents a radical ofthe formula SiR^(a)R^(b)R^(c), or —NR^(a)R^(b), where each of theradicals R^(a) and R^(b) independently of the other represents hydrogenor an optionally substituted hydrocarbon radical and R^(c) independentlyrepresents an optionally substituted hydrocarbon radical, or—NR^(a)R^(b) represents a 3- to 9-membered heterocycle which, inaddition to this nitrogen atom, may contain one or two further ringheteroatoms from the group consisting of N, O and S and which issubstituted or unsubstituted, or represents a radical of the formula—C(═O)—R^(e) or —P(═O)(R^(f))₂, where R^(e) and both radicals R^(f) ineach case independently of one another are selected from the groupconsisting of hydrogen, OH, unsubstituted or substituted (C₁-C₈)alkyl,unsubstituted or substituted (C₁-C₄)haloalkyl, unsubstituted orsubstituted (C₂-C₈)alkenyl, unsubstituted or substituted (C₂-C₈)alkynyl,unsubstituted or substituted (C₁-C₆)alkoxy, unsubstituted or substituted(C₁-C₆)alkoxy-(C₁-C₈)alkyl, unsubstituted or substituted(C₁-C₄)haloalkoxy, unsubstituted or substituted(C₁-C₄)haloalkoxy-(C₁-C₈)alkyl, unsubstituted or substituted(C₃-C₈)alkenyloxy, unsubstituted or substituted(C₃-C₈)alkenyloxy-(C₁-C₈)alkyl, unsubstituted or substituted(C₃-C₈)alkynyloxy, unsubstituted or substituted(C₃-C₈)alkynyloxy-(C₁-C₈)alkyl, unsubstituted or substituted —NR*R**,where R* and R** are as defined above, unsubstituted or substitutedtri-[(C₁-C₄)alkyl]silyl, unsubstituted or substitutedtri-[(C₁-C₄)alkyl]silyl-(C₁-C₈)alkyl, unsubstituted or substituted(C₃-C₆)cycloalkyl, unsubstituted or substituted(C₃-C₆)cycloalkyl-(C₁-C₈)alkyl, unsubstituted or substituted(C₅-C₆)cycloalkenyl, unsubstituted or substituted(C₅-C₆)cycloalkenyl-(C₁-C₈)alkyl, unsubstituted or substituted(C₅-C₆)cycloalkynyl, unsubstituted or substituted(C₅-C₆)cycloalkynyl-(C₁-C₈)alkyl, unsubstituted or substituted phenyl,unsubstituted or substituted phenyl-(C₁-C₈)alkyl, unsubstituted orsubstituted phenoxy, unsubstituted or substituted phenoxy-(C₁-C₈)alkyl,unsubstituted or substituted phenylamino, unsubstituted or substitutedphenylamino(C₁-C₈)alkyl, unsubstituted or substituted Het, unsubstitutedor substituted Het-(C₁-C₆)alkyl and unsubstituted or substitutedHet-O—(C₁-C₆)alkyl, where Het in each case represents a saturated,partially unsaturated or heteroaromatic monocyclic heterocyclyl radicalhaving 3 to 9 ring atoms or a 9- or 10-membered bicyclic heterocycle ineach case containing 1, 2, 3 or 4 heteroatoms selected from the groupconsisting of 0, N and S, where each of the specified substitutedradicals is substituted in the acyclic moiety by one or more identicalor different radicals R^(A) and/or where each of the specifiedsubstituted radicals is substituted in the cyclic moiety by one or moreidentical or different radicals R^(B), where R^(A) represents halogen,cyano, hydroxy or (C₁-C₆)alkoxy, and R^(B) independently of any furtherradicals R^(B) present is selected from the group consisting of halogen,cyano, hydroxy, oxo, nitro, (C₁-C₈)alkyl, (C₁-C₆)haloalkyl,cyano-(C₁-C₆)alkyl, hydroxy-(C₁-C₆)alkyl, nitro-(C₁-C₆)alkyl,(C₂-C₈)alkenyl, (C₂-C₈)haloalkenyl, (C₂-C₈)alkynyl, (C₂-C₈)haloalkynyl,(C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy, (C₂-C₈)alkinyloxy, (C₁-C₈)haloalkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₄)alkoxy,(C₁-C₆)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₄)alkoxy,(C₁-C₈)alkylthio, (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio,(C₁-C₈)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl, (C₁-C₈)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl,—NR*R**, tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-(C₁-C₈)alkyl,(C₃-C₈)cycloalkyl-(C₁-C₈)alkoxy, phenyl, phenyl-(C₁-C₈)alkyl, phenoxy,phenoxy-(C₁-C₈)alkyl, phenylamino, phenylamino-(C₁-C₈)alkyl or a 5- or6-membered monocyclic or 9- or 10-membered bicyclic heterocyclecontaining 1, 2, 3 or 4 heteroatoms selected from the group consiting ofO, N and S, where each of these specified radicals can be substituted inthe cyclic moiety by one or more identical or different R^(bb), whereR^(aa) in each case independently of one another represent hydrogen, OH,(C₁-C₈)alkyl, (C₁-C₆)haloalkyl, (C₂-C₈)alkenyl, (C₂-C₈)alkynyl,(C₁-C₈)alkoxy, (C₁-C₆)alkoxy-(C₁-C₆)alkyl,(C₁-C₆)alkoxy-(C₁-C₆)alkyloxy, (C₁-C₆)haloalkoxy,(C₁-C₆)haloalkoxy-(C₁-C₆)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₆)alkoxy,(C₃-C₈)alkenyloxy, (C₃-C₈)alkenyloxy-(C₁-C₆)alkyl,(C₃-C₈)alkenyloxy-(C₁-C₆)alkoxy, (C₃-C₈)alkynyloxy,(C₃-C₈)alkynyloxy-(C₁-C₆)alkyl, (C₃-C₈)alkynyloxy-(C₁-C₆)alkoxy,—NR*R**, tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkoxy, (C₃-C₈)cycloalkyl,(C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-(C₁-C₈)alkyl,(C₃-C₈)cycloalkyl-(C₁-C₈)alkoxy, (C₅-C₈)cycloalkenyl,(C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl, (C₅-C₈)cycloalkenyloxy,(C₅-C₈)cycloalkynyl, (C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl,(C₅-C₈)cycloalkynyl-(C₁-C₆)alkoxy, phenyl, phenyl-(C₁-C₈)alkyl,phenyl-(C₁-C₈)alkoxy, phenoxy, phenoxy-(C₁-C₈)alkyl,phenoxy-(C₁-C₈)alkoxy, phenylamino, phenylamino-(C₁-C₈)alkyl,phenylamino-(C₁-C₈)alkoxy or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms andoptionally bonded via an alkylene group or an alkoxy group is selectedfrom the group consisting of O, N and S, where each of the radicalsR^(aa) encompassing a cycle is optionally substituted in the cyclicmoiety by one or more identical or different radicals R^(bb), and whereR*, R**, —NR*R** and R^(bb) have the meaning given above.
 7. Thecompound of the formula (I) or salt thereof as claimed in claim 1,wherein R¹ represents hydrogen, unsubstituted (C₁-C₁₈)alkyl,unsubstituted (C₂-C₁₈)alkenyl, unsubstituted (C₂-C₁₈)alkynyl,substituted (C₁-C₁₈)alkyl, substituted (C₂-C₁₈)alkenyl or substituted(C₂-C₁₈)alkynyl, where in the case of substituted (C₁-C₁₈)alkyl,substituted (C₂-C₁₈)alkenyl and substituted (C₂-C₁₈)alkynyl thesubstituent(s) is/are each independently of one another selected fromgroups (a)-(e) below: (a) halogen, cyano, thio, nitro, hydroxy, carboxy,(C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy, (C₂-C₈)alkynyloxy, (C₁-C₈)haloalkoxy,(C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₈)alkylthio, (C₂-C₈)alkenylthio,(C₂-C₈)alkyinylthio, (C₁-C₈)haloalkylthio, (C₂-C₈)haloalkenylthio,(C₂-C₈)haloalkinylthio, (C₁-C₈)alkylsulfinyl, (C₂-C₈)alkenylsulfinyl,(C₂-C₈)alkynylsulfinyl, (C₁-C₈)haloalkylsulfinyl,(C₂-C₈)haloalkenylsulfinyl, (C₂-C₈)haloalkinylsulfinyl,(C₁-C₈)alkylsulfonyl, (C₂-C₈)alkenylsulfonyl, (C₂-C₈)alkynylsulfonyl,(C₁-C₈)haloalkylsulfonyl, (C₂-C₈)haloalkenylsulfonyl,(C₂-C₈)haloalkynylsulfonyl, —NR*R**, where R*, R** and —NR*R** in eachcase have the meaning given above, (b) (C₃-C₈)cycloalkyl,(C₅-C₈)cycloalkenyl, (C₅-C₈)cycloalkinyl,(C₃-C₈)cycloalkyl-(C₁-C₆)alkoxy,(C₃-C₈)cycloalkyl-(C₁-C₆)alkyl-S(O)_(p)—,(C₅-C₈)cycloalkenyl-(C₁-C₆)alkoxy,(C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl-S(O)_(p)—,(C₅-C₈)cycloalkynyl-(C₁-C₆)alkoxy,(C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl-S(O)_(p)—, (C₃-C₈)cycloalkoxy,(C₃-C₈)cycloalkyl-S(O)_(p)—, (C₅-C₈)cycloalkenyloxy,(C₅-C₈)cycloalkenyl-S(O)_(p)—, (C₅-C₈)cycloalkynyloxy,(C₅-C₈)cycloalkynyl-S(O)_(p)—, (C₃-C₈)cycloalkoxy-(C₁-C₆)alkoxy,(C₃-C₈)cycloalkoxy-(C₁-C₆)alkyl-S(O)_(p)—, phenyl, phenyl(C₁-C₆)alkoxy,phenoxy, phenyl-S(O)_(p)—, phenyl-(C₁-C₆)alkyl-S(O)_(p)—,phenoxy-(C₁-C₆)alkoxy, phenoxy-(C₁-C₆)alkyl-S(O)_(p)—, a radical Het¹,Het¹-S(O)_(p)—, Het¹-(C₁-C₆)alkoxy, Het¹-O—, Het¹-O—(C₁-C₆)alkoxy, wherethe radical Het¹ has the meaning given above, and where each of thelast-mentioned radicals of the group (b) in the acyclic moiety isunsubstituted or substituted by one or more identical or differentradicals selected from the group consisting of halogen, cyano, hydroxyand (C₁-C₆)alkoxy, and/or in the cyclic moiety is unsubstituted orsubstituted by one or more identical or different radicals R^(B), whereR^(B) independently of any further radicals R^(B) present is selectedfrom the group consisting of halogen, cyano, hydroxy, oxo, nitro,(C₁-C₈)alkyl, (C₁-C₆)haloalkyl, cyano-(C₁-C₆)alkyl,hydroxy-(C₁-C₆)alkyl, nitro-(C₁-C₆)alkyl, (C₂-C₈)alkenyl,(C₂-C₈)haloalkenyl, (C₂-C₈)alkynyl, (C₂-C₈)haloalkynyl, (C₁-C₈)alkoxy,(C₂-C₈)alkenyloxy, (C₂-C₈)alkinyloxy, (C₁-C₈)haloalkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₄)alkoxy,(C₁-C₆)haloalkoxy-(C₁-C₄)alkyl, (C₁-C₆)haloalkoxy-(C₁-C₄)alkoxy,(C₁-C₈)alkylthio, (C₂-C₆)alkenylthio, (C₂-C₆)alkynylthio,(C₁-C₈)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl, (C₁-C₈)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)alkyl,—NR*R**, tri-[(C₁-C₄)alkyl]silyl, tri-[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,(C₃-C₈)cycloalkyl, (C₃-C₈)cycloalkoxy, (C₃-C₈)cycloalkyl-(C₁-C₈)alkyl,(C₃-C₈)cycloalkyl-(C₁-C₈)alkoxy, phenyl, phenyl-(C₁-C₈)alkyl, phenoxy,phenoxy-(C₁-C₈)alkyl, phenylamino, phenylamino-(C₁-C₈)alkyl or a 5- or6-membered monocyclic or 9- or 10-membered bicyclic heterocyclecontaining 1, 2, 3 or 4 heteroatoms selected from the group consiting ofO, N and S, where each of these specified radicals can be substituted inthe cyclic moiety by one or more identical or different R^(bb), and theindex p is in each case 0, 1 or 2, (c) —C(═O)—R^(C), —C(═O)—O—R^(C),—O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C), —C(═S)—S—R^(C),—C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C),—N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),—P(═O)(OR^(c))(R^(D)), —P(═O)(OR^(c))(OR^(D)) or—O—P(═O)(OR^(C))(OR^(D)), where R*, R** and —NR*R** in each case havethe meaning given above and R^(c) and R^(D) are as defined below, (d)—SiR′₃, —O—SiR′₃, (R′)₃Si—(C₁-C₆)alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂,—O—NR′₂, —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR′)₂, in which each of theradicals R′ is independently selected from the group consisting of H,(C₁-C₄)alkyl or phenyl which is unsubstituted or substituted by one ormore radicals from the group consisting of halogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy and nitro orsubstituted at two adjacent positions by a (C₂-C₆)alkylene bridge, andthe index q represents an integer from 0 to 6, and (e)R″O—CHR′″CH(OR″)—(C₁-C₆)alkoxy, in which each of the radicals R″independently of the others represents H or (C₁-C₄)-alkyl or togetherthe radicals represent a (C₁-C₆)-alkylene group and R′″ represents H or(C₁-C₄)-alkyl, or R¹ represents (C₃-C₉)cycloalkyl, (C₅-C₉)cycloalkenyl,(C₅-C₉)cycloalkynyl or phenyl, where each of these radicals isunsubstituted or substituted by one or more radicals from the groupconsisting of the radicals of subgroups (a′)-(e′) below: (a′) halogen,cyano, thio, nitro, hydroxy, carboxy, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,(C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₂-C₈)alkenyl, (C₂-C₈)haloalkenyl,(C₂-C₈)alkynyl, (C₂-C₈)haloalkynyl, (C₁-C₈)alkoxy, (C₂-C₈)alkenyloxy,(C₂-C₈)alkynyloxy, (C₁-C₈)haloalkoxy, (C₁-C₄)alkoxy-(C₁-C₄)alkoxy,(C₁-C₈)alkylthio, (C₂-C₈)alkenylthio, (C₂-C₈)alkynylthio and —NR*R**,where R*, R**, —NR*R**, and R^(bb) in each case have the meaning givenabove, (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),—O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C), —C(═S)—S—R^(C),—C(═O)—NR*R**, —C(═O)—O—NR*R**, —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C),—N(R*)—C(═O)—NR*R**, —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),—P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) or—O—P(═O)(OR^(C))(OR^(D)), where R*, R**, —NR*R** and R^(bb) in each casehave the meaning given above and R^(C) and R^(D) have the meaningdefined below, (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,(R′)₃Si—(C₁-C₆)alkoxy, —CO—O—NR′2, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,—CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR′)₂, in which each of the radicals R′independently of the others represents H, (C₁-C₄)-alkyl or phenyl whichis unsubstituted or substituted by one or more radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy and nitro or is substituted at two adjacent positionsby a (C₂-C₆)-alkylene bridge, and q represents an integer from 0 to 6,and (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)alkoxy, inwhich each of the radicals R″ independently of the others represents Hor (C₁-C₄)-alkyl or together the radicals represent a (C₁-C₆)-alkylenegroup and R′″ represents H or (C₁-C₄)-alkyl, and (e′) a radical of theformula Het¹ which is unsubstituted or substituted by one or moreidentical or different radicals R^(B), where R^(B) has the meaning givenabove, or R¹ represents a polycyclic radical based on (C₃-C₉)cycloalkyl,(C₅-C₉)cycloalkenyl, (C₅-C₉)cycloalkynyl or phenyl, where the base ringis fused with a carbocyclic or heterocyclic ring, and where the basering or the polycyclic system is unsubstituted or substituted by one ormore identical or different radicals R^(B), where R^(B) has the meaninggiven above, or R¹ represents a heterocyclic radical Het¹ which isunsubstituted in the ring or in the polycyclic system or substituted byone or more identical or different radicals R^(B), where R^(B) has themeaning given above, where Het¹ in each case independently of the othersis a saturated, partially unsaturated or heteroaromatic monocyclicheterocyclyl radical having 3 to 9 ring atoms, or a 9- or 10-memberedbicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected fromthe group consisting of O, N and S, R^(A) represents halogen, cyano,hydroxy or (C₁-C₆)alkoxy, R^(B) has the meaning given above, R^(C) andR^(D) each independently of one another (and also independently ofradicals R^(C), R^(D) in other groups) represent a radical selected fromthe group consisting of: (i) hydrogen, unsubstituted (C₁-C₈)alkyl,unsubstituted (C₂-C₈)alkenyl, unsubstituted (C₂-C₈)alkynyl, substituted(C₁-C₈)alkyl, substituted (C₂-C₈)alkenyl, or substituted (C₂-C₈)alkynyl,where each of these substituted radicals is substituted by one or moreradicals from the group halogen, cyano, nitro, hydroxy, (C₁-C₆)alkoxy,(C₂-C₆)alkenyloxy, (C₂-C₆)alkynyloxy, (C₁-C₈)haloalkoxy,(C₁-C₄)alkoxy-(C₁-C₄)alkoxy, (C₁-C₈)alkylthio, (C₁-C₈)haloalkylthio,(C₁-C₈)alkylsulfinyl, (C₁-C₈)haloalkylsulfinyl, (C₁-C₈)alkylsulfonyl,(C₁-C₈)haloalkylsulfonyl and tri-[(C₁-C₄)alkyl]silyl, and (ii)(C₃-C₈)cycloalkyl, (C₅-C₈)cycloalkenyl, (C₅-C₈)cycloalkynyl, phenyl,(C₃-C₈)cycloalkyl-(C₁-C₆)alkyl, (C₅-C₈)cycloalkenyl-(C₁-C₆)alkyl,(C₅-C₈)cycloalkynyl-(C₁-C₆)alkyl, phenyl-(C₁-C₆)alkyl,(C₃-C₈)cycloalkyloxy-(C₁-C₆)alkyl,(C₃-C₈)cycloalkyl-S(O)_(p)—(C₁-C₆)alkyl,(C₅-C₈)cycloalkenyloxy-(C₁-C₆)alkyl,(C₅-C₈)cycloalkynyloxy-(C₁-C₆)alkyl, phenoxy-(C₁-C₆)alkyl,phenyl-S(O)_(p)—(C₁-C₆)alkyl, (C₃-C₈)cycloalkylamino-(C₁-C₆)alkyl,(C₅-C₈)cycloalkenylamino-(C₁-C₆)alkyl,(C₅-C₈)cycloalkynylamino-(C₁-C₆)alkyl, phenylamino-(C₁-C₆)alkyl, Het¹,Het¹-(C₁-C₆)alkyl, Het¹-O—(C₁-C₆)alkyl or Het¹-S(O)_(p)—(C₁-C₆)alkyl,where Het¹ has the meaning given above, and where each of these radicalsis unsubstituted in the acyclic moiety or substituted by one or moreidentical or different radicals R^(A) and in the cyclic moiety isunsubstituted or substituted by one or more identical or differentradicals R^(B) and p in each case represents 0, 1 or 2, where R^(A) andR^(B) in each case have the meaning given above, R^(aa) has the meaninggiven above, and where R^(aa) preferably independently is a radicalselected from the group consisting of hydrogen, OH, (C₁-C₆)alkyl,(C₁-C₄)haloalkyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₁-C₆)alkoxy,(C₁-C₆)alkoxy-(C₁-C₆)alkyl, (C₁-C₆)alkoxy-(C₁-C₆)alkyloxy,(C₁-C₄)haloalkoxy, (C₁-C₄)haloalkoxy-(C₁-C₆)alkyl,(C₁-C₄)haloalkoxy-(C₁-C₆)alkoxy, (C₃-C₆)alkenyloxy,(C₃-C₆)alkenyloxy-(C₁-C₆)alkyl, (C₃-C₆)alkenyloxy-(C₁-C₆)alkoxy,(C₃-C₆)alkynyloxy, (C₃-C₆)alkynyloxy-(C₁-C₆)alkyl,(C₃-C₆)alkynyloxy-(C₁-C₆)alkoxy, —NR*R**, where R* and R** are asdefined above, tri[(C₁-C₄)alkyl]silyl,tri[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkyl,tri[(C₁-C₄)alkyl]silyl-(C₁-C₆)alkoxy, (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkoxy, (C₃-C₆)cycloalkyl-(C₁-C₈)alkyl,(C₃-C₆)cycloalkyl-(C₁-C₈)alkoxy, (C₅-C₆)cycloalkenyl,(C₅-C₆)cycloalkenyl-(C₁-C₆)alkyl, (C₅-C₆)cycloalkenyloxy,(C₅-C₆)cycloalkynyl, (C₅-C₆)cycloalkynyl-(C₁-C₆)alkyl,(C₅-C₆)cycloalkynyl-(C₁-C₆)alkoxy, phenyl, phenyl-(C₁-C₆)alkyl,phenyl-(C₁-C₆)alkoxy, phenoxy, phenoxy-(C₁-C₆)alkyl,phenoxy-(C₁-C₆)alkoxy, phenylthio, phenyl-S(O)_(p)—(C₁-C₆)alkyl,phenyl-S(O)_(p)—(C₁-C₆)alkoxy, where p in each case independently of oneanother is 0, 1 or 2, phenylamino, phenylamino-(C₁-C₆)alkyl,phenylamino-(C₁-C₆)alkoxy or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle optionally bonded via an alkylene groupor an alkoxy group, containing 1, 2, 3 or 4 heteroatoms selected fromthe group consisting of O, N and S, where each of the specified cyclicradicals R^(aa) in the cyclic moiety is optionally substituted by one ormore identical or different radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and(C₁-C₄)haloalkoxy.
 8. The compound of the formula (I) or salt thereof asclaimed in claim 1, wherein (R²)_(n) represents n substituents R², whereR² (if n=1) or each of the substituents R² (if n is greater than 1)independently of the others represents halogen, cyano, nitro,(C₁-C₆)alkyl, (C₁-C₆)alkoxy, (C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl,(C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkyl, (C₂-C₆)haloalkenyl,(C₁-C₆)haloalkoxy, (C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,tri[(C₁-C₄)alkyl]silyl or tri[(C₁-C₄)alkyl]silyl-(C₁-C₄)alkyl, and/or(R³)_(m) represents m substituents R³, where R³ (if m=1) or each of thesubstituents R³ (if m is greater than 1) independently of one anotherrepresents halogen, cyano, nitro, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,(C₁-C₆)alkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)halo alkyl, (C₂-C₆)halo alkenyl, (C₁-C₆)haloalkoxy,(C₁-C₆)haloalkylthio, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, NR*R**,tri[(C₁-C₄)alkyl]silyl or tri[(C₁-C₄)alkyl]silyl(C₁-C₄)alkyl or where ineach case two groups R³ directly adjacent on the ring together representa group of the formula —Z³-A**-Z⁴—, in which A** represents an alkylenegroup having 1 to 4 carbon atoms which is optionally substituted by oneor more radicals from the group consisting of halogen, (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and (C₁-C₄)haloalkoxy, Z³ represents adirect bond, O or S and Z⁴ represents a direct bond, O or S, where thegroup —Z³-A**—Z⁴ together with the carbon atoms, bonded to the group, ofthe phenyl ring form a fused-on 5- or 6-membered ring, R*, R** eachindependently of one another or together with the nitrogen atom have themeaning mentioned above and n, m in each case independently of oneanother represent 0, 1, 2, 3, 4 or
 5. 9. The compound of the formula (I)or salt thereof as claimed in claim 1, wherein (R²)_(n) represents nsubstituents R², where, in the case that n=1, the substituent R² or, inthe case that n is greater than 1, each of the substituents R²independently of the others represents halogen, cyano, nitro,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl,(C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₂-C₄)alkenyl, (C₂-C₄)alkynyl,tri[(C₁-C₄)alkyl]silyl or tri[(C₁-C₄)alkyl]silyl(C₁-C₄)alkyl, and nrepresents 0, 1, 2, 3, or
 4. 10. The compound of the formula (I) or saltthereof as claimed in claim 1, wherein (R³)_(m) represents msubstituents R³, where in the case that m=1, the substituent R³ or, inthe case that m is greater than 1, each of the substituents R³independently of one another represents halogen, cyano, nitro,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkyl, (C₂-C₄)haloalkenyl,(C₁-C₄)haloalkoxy, (C₁-C₄)haloalkylthio, (C₁-C₄)haloalkylsulfinyl,(C₁-C₄)haloalkylsulfonyl, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl ortri[(C₁-C₄)alkyl]silyl-Z^(b)—, where Z^(b)=is a covalent bond or(C₁-C₄)alkylene, or in each case two groups R³ directly adjacent to oneanother at the ring together represent a group of the formula—Z³-A**-Z⁴—, where A** represents an alkylene group which is optionallysubstituted by one or more radicals from the group halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and (C₁-C₄)haloalkoxy, Z³represents O or S and Z⁴ represents O or S, where the group —Z³-A**-Z⁴—together with the carbon atoms, attached to the group, of the phenylring form a fused-on 5- or 6-membered ring, m represents 0, 1, 2, 3, 4or
 5. 11. The compound of the formula (I) or salt thereof as claimed inclaim 1, wherein (R²)_(n) represents n substituents R², where, in thecase that n=1, the substituent R² or, in the case that n is greater than1, each of the substituents R² independently of one another representsfluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl,methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl,trifluoromethoxy, trifluoroalkylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl, and (R³)_(m) represents m substituents R³,where, in the case that m=1, the substituent R³ or, in the case that mis greater than 1, each of the substituents R³ independently of theothers represents fluorine, chlorine, bromine, iodine, cyano, nitro,methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl,trifluoromethyl, trifluoromethoxy, trifluoroalkylthio,trifluoromethylsulfinyl or trifluoromethylsulfonyl, and m represents 0,1, 2, 3 or 4, and n represents 0, 1, 2 or
 3. 12. The compound of theformula (I) or salt thereof according to claim 1, wherein Q represents aheteroaromatic radical selected from the group consisting of pyridinyl,pyrazinyl, thienyl and thiazolyl; and R¹ is selected from the groupconsisting of hydrogen, acetyl, propanoyl, butanoyl, pentanoyl,hexanoyl, 2-methylpropanoyl, 2,2-difluoroacetyl, 2,2,2-trifluoroacetyl,C(═O)OMe, cyclopropanecarbonyl, 1-methylcyclopropanecarbonyl, acryl,prop-2-ynoyl, but-2-ynoyl, 2-methylacryl, benzoyl, 4-chlorobenzoyl,3-chlorobenzoyl, 2-chlorobenzoyl, 4-fluorobenzoyl, 3-fluorobenzoyl,2-fluorobenzoyl, 2,2-dimethylpropanoyl, 3,3-dimethylbutanoyl,2-nitrobenzoyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl,2,2-dichloroacetyl, 2-methoxyacetyl, 2,6-difluorobenzoyl, C(O)C(═O)OMeand C(O)CH₂C(O)OMe.
 13. The compound of the formula (I) or salt thereofaccording to claim 5, wherein R1 represents hydrogen or a hydrolyzableradical having in 1 to 20 carbon atoms.
 14. A herbicidal or plantgrowth-regulating composition, wherein the composition comprises one ormore compounds of the formula (I) or salts thereof as defined in claim1, and one or more further substances selected from groups (i) and/or(ii): (i) one or more further agrochemically active substances, (ii) oneor more formulation auxiliaries customary in crop protection.
 15. Thecomposition according to claim 14, wherein the one or more furtheragrochemically active substances are selected from the group consistingof insecticides, acaricides, nematicides, further herbicides,fungicides, safeners, fertilizers and further growth regulators.
 16. Amethod for controlling harmful plants or for regulating the growth ofplants, comprising applying an effective amount of one or more compoundsof the formula (I) or salts thereof, as defined in claim 1, or acomposition thereof, to the plants, seeds of plants, the soil in whichor on which the plants grow or an area under cultivation.
 17. A processfor preparing a compound of the formula (I) or a salt thereof as definedin claim 1, comprising converting a compound of the formula (E)

by reduction into a compound of the formula (Ia)

and the compound (Ia) is optionally reacted further to give a compoundof the formula (I), wherein R¹ in formula (I) does not representhydrogen, where R represents hydrogen or a hydrolysable radical.